Ethanol → 4-Benzyloxy-2,2-dihydroxymethylbutanol

HRID 514633Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:22][OH:23])([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(O)C>CO>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([CH2:17][OH:18])([CH2:22][OH:23])[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

1.03 g (3.24 mmol equivalents) of diethyl 2-(2-benzyloxyethyl)-2-hydroxymethylmalonate was dissolved in 10 mL of methanol, and this was added dropwise to 1.69 g (44.6 mmol equivalents) of sodium borohydride over 20 minutes. This was refluxed while heating overnight and then cooled to room temperature (25° C.). Water was added to the reaction liquid, and a reaction was carried out for 30 minutes. The reaction liquid was washed with chloroform, and the aqueous phase was concentrated under vacuum. 100 mL of ethanol was added to the obtained residue, and the mixture was refluxed while heating for 2 hours. Immediately after completion of the reaction, the mixture was subjected to silica gel column chromatography (eluent: ethanol) to give 543 mg of 4-benzyloxy-2,2-dihydroxymethylbutanol as an crude product.

Workup

temperatureThis was refluxed
temperaturewhile heating overnight
customThe reaction liquid
washwas washed with chloroform
concentrationthe aqueous phase was concentrated under vacuum
addition100 mL of ethanol was added to the obtained residue
temperaturethe mixture was refluxed
temperaturewhile heating for 2 hours
customImmediately after completion of the reaction

Sources & evidence

ORD record: ord-306cb0c3294e4c209de3d65c3499c984
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09107964B2

Reaction notes

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