Sodium borohydride → (4-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)methanol

HRID 1255268Notes

Reaction equation

[BH4-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:18]=[O:19])[S:16][CH:17]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>C(O)C>[Si:3]([O:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH2:18][OH:19])[S:16][CH:17]=1)([C:6]([CH3:8])([CH3:9])[CH3:7])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium borohydride (1.40 g) was added portionwise to a stirred solution at 0° C. of 4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophene-2-carbaldehyde [Aromatic Intermediate 6] (10 g) in ethanol (70 mL). The reaction mixture was stirred for 1 hour at 0° C. and then partitioned between ethyl acetate and aqueous brine and separated. The organic layer was dried, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 12% ethyl acetate in isohexane as solvent. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 6.00 g.

Workup

custompartitioned between ethyl acetate and aqueous brine
customseparated
customThe organic layer was dried
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe crude product was purified by flash silica chromatography
additionFractions containing the product
customwere evaporated to dryness

Sources & evidence

ORD record: ord-364a4037f94d411f9dccfbc4bf5b0ce8
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455483B2

Reaction notes

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