Water → HCID 12551980, compound

HRID 2080106Notes

Reaction equation

HRID 2080106 reaction equation
[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>C(O)C>[C:1]1([S:7][C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22607995HCID 22607995, compound

Product 1

HCID 12551980HCID 12551980, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Phenylsulfanyl-benzaldehyde described in Preparation Example 92 (321 mg, 1.49 mmol) was dissolved in ethanol (6 mL), sodium borohydride (113 mg, 2.98 mmol) was added thereto at 0° C., followed by stirring at room temperature for 3 hours. Water was added to the reaction solution, 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 (220 mg, 1.02 mmol, 68%) was obtained as a colorless oil.

Workup

  1. customat 0° C.
  2. extractionwas then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-ae07112b73bf43ef86ecd8cff5f4cfa7
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…