3-Furanmethanol

Colorless to light yellow liqui

To a solution of ethyl 3-furoate (7) (4.00 g, 28.5 mmol) in Et0°C , water (15mL) added 3 aldehyde 4 (14.1g, purity 97percent, 147mmol) in ether (150mL) solution, with vigorous stirring added Sodium borohydride (8.94g, 235mmol), the addition was completed, brought to room temperature stirring was continued for 0.5h, the raw material disappeared; adding water, the upper ether layer was separated, the aqueous layer was extracted three times with ether, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed distillation diethyl ether; the remaining liquid was distilled under reduced pressure to give a colorless liquid 5 (13.96g, 99percent).General procedure: FFR (99percent, Sigma-Aldrich) 1 mL and various amounts of thenickel catalysts were added to 30 mL of a solvent (methanol(99.8percent, Duksan), ethanol, IPA, or methyl isobutyl ketone (MIBK;99.5percent, TCI)). Raney Ni (Ni 92.5percent, TCI) was washed with ethanoland distilled water twice each and dried in a vacuum oven at50 °C before use. The mixed solution was placed in a 100 mL Teflonliner with a magnetic stir-bar and sealed in a stainless steel autoclave.Then the reactor was purged with H2 three times to excludeother gases. The autoclave was heated to 110 °C at which temperaturethe hydrogenation reaction was performed under 30 bar H2and stirring at 700 rpm. After the reaction, the autoclave wascooled, and the solution was subsequently centrifuged at11, 000 rpm for 10 min to separate the liquid-phase products fromthe catalyst. For the recycling tests, 1 mL of FFR and 30 mL of IPAwere added to the centrifuged Ni catalyst without any furthertreatment. The products were analyzed by a gas chromatograph(GC; YL 6100) equipped with a capillary column (DB-624, AgilentTechnologies, 30 m 0.53 mm 3.00 lm) and flame ionizationdetector (FID).The selective hydrogenation of various unsaturated aldehydesand ketones was performed according to the following protocol.The reactant 1 mL (3-cyclohexene-1-carboxaldehyde (97percent, Sigma-Aldrich), 5-hydroxymethyl-2-furaldehyde (99percent, Sigma-Aldrich), 5-methylfurfural (99percent, Sigma-Aldrich), 2-thiophenecarboxaldehyde (98percent, Sigma-Aldrich), pyrrole-2-carboxaldehyde (98percent, Sigma-Aldrich), 3-furancarboxaldehyde(P97percent, Sigma-Aldrich), 2-furyl methyl ketone (99percent, Sigma-Aldrich), acetophenone (99percent, Sigma-Aldrich), cinnamaldehyde(99percent, Sigma-Aldrich), or trans-2-hexen-1-al (98percent, Sigma-Aldrich))was added to 30 mL of IPA. The 6.8 nm Ni nanoparticle catalyst(20 mg) was charged to the reactor. The hydrogenation reactionswere then performed according to the FFR hydrogenation protocol, except the reaction temperature was 100 °C for 3-cyclohexene-1-carboxaldehyde.General procedure: Preparation of 1, 2-di(fur-3-yl) was carried out via procedures similar to those used for the preparation of 1n, and all of the experimental procedures are summarized as follows: Reduction of furan-3-carboxaldehyde: 0.02 mol of furan-3-carboxaldehyde was used as the starting material to synthesize (fur-3-yl)-methanol (92percent yield). Chlorination of (fur-3-yl)methanol: 0.01 mol of (fur-3-yl)methanol was used as the starting material to synthesize (fur-3-yl)methyl chloride, without characterization. Wittig Reaction: 24 mmol of triphenylphosphine and 20 mmol of (fur-3-yl)methyl chloride were used to synthesize triphenylphosphonium salt. Then, 10 mmol of the triphenylphosphonium salt, 11 mmol of 3-fural, and all of the other necessary reagents were used to synthesize cis- and trans-1, 2-di(fur-3-yl)ethene 1p, obtaining a total yield 32percent. The cis and trans forms were purified via silica gel chromatography using hexane for characterization.A suspension of LiAlH

Molecular Weight:98.10
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:98.036779430
Monoisotopic Mass:98.036779430
Topological Polar Surface Area:33.4
Heavy Atom Count:7
Complexity:54
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes