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

HRID 2279957
Notes
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Reaction equation

HRID 2279957 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 112772515-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehyde

Product 1

HCID 57989124(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methanolYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. concentrationThe reaction solution was concentrated in vacuo
  2. custompartitioned between ethyl acetate (30 mL) and brine (30 mL)
  3. filtrationfiltered
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes