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

HRID 446392Notes

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-6b9051f2312946c79a0db3d9461b4f8d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476265B2

Reaction notes

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