Sodium borohydride → (5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methanol

HRID 2279957Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14]([CH:16]=[O:17])=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14]([CH2:16][OH:17])=[CH:13][CH:12]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]thiophene-2-carbaldehyde (17.8 g, 66.1 mmol) in ethanol (180 mL) at 0° C. was added sodium borohydride (2.5 g, 66.1 mmol). The resulting solution was stirred at 0° C. for 1.5 h. The reaction solution was concentrated in vacuo and partitioned between ethyl acetate (30 mL) and brine (30 mL). The organic phase was over sodium sulphate, filtered and concentrated in vacuo to give the title compound as a yellow oil (17.5 g, 97%) which was used in the next step without further purification.

Workup

concentrationThe reaction solution was concentrated in vacuo
custompartitioned between ethyl acetate (30 mL) and brine (30 mL)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-37e18061e48e4fd6916b5894870ddf5a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133185B2

Reaction notes

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