Water → 3-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]prop-2-en-1-ol

HRID 238294Notes

Reaction equation

HRID 238294 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:13]=[CH:14][CH:15]=[O:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH:13]=[CH:14][CH2:15][OH:16])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 714275833-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]prop-2-enal

Product 1

HCID 688230923-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

692 mg (2.97 mmol) of 3-(4-(4-fluorophenyl)thiazol-2-yl)propenal and 224.5 mg (5.93 mmol) of sodium borohydride were stirred in 50 ml of ethanol at room temperature for 3 h. Water was added, and the mixture was concentrated. The residue was taken up with water and ethyl acetate. The organic phase was separated and evaporated. The residue was purified by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA). Yield: 280 mg (40%).

Workup

  1. concentrationthe mixture was concentrated
  2. customThe organic phase was separated
  3. customevaporated
  4. customThe residue was purified by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA)

Sources & evidence

ORD record
ord-20b6517f8d484e27b29dfcc1b2b76b12
Source dataset
uspto-grants-2014_02
Patent number
US08642620B2

Reaction notes

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