Water → HCID 23130490, compound

HRID 2080124Notes

Reaction equation

HRID 2080124 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[S:9][C:8]([CH:10]=[O:11])=[CH:7][CH:6]=1.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[S:9][C:8]([CH2:10][OH:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23130549HCID 23130549, compound

Product 1

HCID 23130490HCID 23130490, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(2-Fluoro-benzyl)-thiophene-2-carbaldehyde described in Preparation Example 123 (2.81 g, 12.7 mmol) was dissolved in ethanol (40 mL), sodium borohydride (964 mg, 25.4 mmol) was added at 0° C., and the solution was stirred at room temperature for 1 hour. Water was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (2.10 g, 9.45 mmol, 74%) was obtained as a colorless oil.

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-f591007851694e6fad3cd28b688433f9
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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