Water → [5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-2-thienyl]methanol

HRID 2247735Notes

Reaction equation

HRID 2247735 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH:15]=[O:16])=[C:12]([CH2:17][CH3:18])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[Si:1]([O:8][CH2:9][C:10]1[S:14][C:13]([CH2:15][OH:16])=[C:12]([CH2:17][CH3:18])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 590520075-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethylthiophene-2-carboxaldehyde

Product 1

HCID 68526897[5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-2-thienyl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethylthiophene-2-carboxaldehyde that was obtained in Example 10 (10b) (1.5 g, 5.8 mmol) in methanol (10 mL) were slowly added sodium borohydride (0.22 g, 5.8 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 30 minutes. After stirring, the solvent was evaporated in vacuo. Subsequently, a solution of the residue obtained in ether was poured into water (20 mL) and extracted with ether. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:4 to 3:7) as the eluent to afford the pure title compound (1.4 g) in a yield of 94% as a colourless oily product.

Workup

  1. customat 0° C.
  2. stirringthe resulting mixture was stirred for 30 minutes
  3. stirringAfter stirring
  4. customthe solvent was evaporated in vacuo
  5. customSubsequently, a solution of the residue obtained in ether
  6. extractionextracted with ether
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration
  10. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-046dceb9072b4345b815d6b048ec4696
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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