3-Methyl-3-oxetanemethanol

Clear colorless to pale yellow liquid

ChEBI: (3-Methyl-3-oxetanyl)methanol is a 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol.

Purify the oxetane by fractionation through a glass column [Pattison J Am Chem Soc 79 3455 1957, Corey et al. J Am Chem Soc 106 2736 1984]. [Beilstein 17 III/IV 1128.]

Equipped with a stirrer, a reflux condenser and a thermometer three-necked flask, followed by adding diethyl carbonate 215ml, trimethylolethane 180g and Κ0Η0. Lg. Heated under stirring to 115 ° C, the reaction was refluxed for lh, the means to reflux distillation apparatus, collecting by-product alcohol was distilled, heating was continued and then distilled collecting the fraction 205~210 ° C to give product 3-hydroxymethyl-3 - methyl-oxetane (2) total 128. 2g. The yield was 83.7percent. Its 1HNMR see Figure 2.General procedure: A 1M solution of TBAF in THF (6.73 mL, 6.73 mmol) was added to tert-butyl[(3-methoxyoxetan-3-yl)methoxy]diphenylsilane (2.4 g, 6.73 mmol) in THF (20 mL) at ambient temperature. The resulting solution was stirred for 2 h. The reaction mixture was evaporated to dryness to give a crude product, which was purified by flash silica gel chromatography, eluted with a gradient of 0 to 100percent EtOAc in heptane. Pure fractions were evaporated to dryness to afford(3-methoxyoxetan-3-yl)methanol (0.650 g, 82percent) as a colourless oil.General procedure: A 1M solution of TBAF in THF (6.73 mL, 6.73 mmol) was added to tert-butyl[(3-methoxyoxetan-3-yl)methoxy]diphenylsilane (2.4 g, 6.73 mmol) in THF (20 mL) at ambienttemperature. The resulting solution was stirred for 2 h. The reaction mixture was evaporatedto dryness to give a crude product, which was purified by flash silica gel chromatography, eluted with a gradient of 0 to 100percent EtOAc in heptane. Pure fractions were evaporated todryness to afford (3-methoxyoxetan-3-yl)methanol

3-Methyl-3-oxetanemethanol has been used in the preparation of star-shaped copolymer consisting of a hyperbranched poly(3-methyl-3-oxetanemethanol) core and polytetrahydrofuran arms, pyridyl disulfide-functionalized cyclic carbonate monomer, required for the synthesis of of functional poly(ε-caprolactone) containing pendant pyridyl disulphide groups and δ-lactams. It is used to synthesize octahydroindole alkaloids and γ-butenolides.

Molecular Weight:102.13
XLogP3:-0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:102.068079557
Monoisotopic Mass:102.068079557
Topological Polar Surface Area:29.5
Heavy Atom Count:7
Complexity:66.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes