1-(2,6-Dimethylphenyl)ethanone

General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water–detergent bath at 60 °C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70percent; output power = 70percent) for 10 min. After addition of 10percent (m/v) solution of No.18 NaOH (2 mL) and 10 μL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90percent recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 Å, 70–230 mesh) doped with 10percent of KF (hexanes/DCM 8:2) gave 0.096 g (53percent) of 3fa as a colorless oil.General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water–detergent bath at 60 °C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70percent; output power = 70percent) for 10 min. After addition of 10percent (m/v) solution of No.18 NaOH (2 mL) and 10 μL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90percent recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 Å, 70–230 mesh) doped with 10percent of KF (hexanes/DCM 8:2) gave 0.096 g (53percent) of 3fa as a colorless oil.General procedure: To a 2-5 mL Biotage microwave vial equipped with a stirrer bar was added aryl ketone (1 equiv.), [Cp*IrCl2]2 (2 mol%), the appropriate diol (2.0 equiv.) [or where appropriate alcohol], PhMe (0.25 mL/mmol aryl ketone) and powdered KOH (4.0 equiv.) sequentially in the open atmosphere. The reaction vessel was sealed with a microwave vial cap (containing a Reseal septum) and an Ar balloon was fitted. The vial was heated to 115 C in a preheated oil bath for 24 h and then the mixture was cooled to RT. For details of workup and purification, see experimental methods section.

Molecular Weight:148.20
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:148.088815002
Monoisotopic Mass:148.088815002
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes