Water → α-(Bromomethyl)-5-thiazolemethanol

HRID 724912Notes

Reaction equation

HRID 724912 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][C:5]([C:7]1[S:11][CH:10]=[N:9][CH:8]=1)=[O:6].O>CO>[Br:3][CH2:4][CH:5]([C:7]1[S:11][CH:10]=[N:9][CH:8]=1)[OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 197113152-Bromo-1-(1,3-thiazol-5-yl)ethan-1-one

Product 1

HCID 19711332α-(Bromomethyl)-5-thiazolemethanolYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (38 mg, 1.0 mmol) was added in one portion to a solution of 207 mg (1.0 mmol) of the product from Example 3 in 2 mL of methanol at 0° C. After stirring for 0.75 h, water was added and the mixture extracted three times with diethyl ether. The combined organic phase was washed with brine, dried(MgSO4) and the solvent removed in vacuo. Flash chromatography (silica gel, 30-40% ethyl acetate-hexanes) afforded 130 mg (62%) of the title compound as a colorless oil: 1H NMR (400 MHz, CDCl3) δ8.78 (s, 1H), 7.83 (s, 1H), 5.28-5.24 (m, 1H), 3.70 (dd, 1H, J=10.6, 3.9 Hz), 3.61 (dd, 1H, J=10.6, 7.9 Hz), 2.95 (d, 1H, J=4.3 Hz).

Workup

  1. extractionthe mixture extracted three times with diethyl ether
  2. washThe combined organic phase was washed with brine, dried(MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8862e28a38f84e3bb47d16712fc4e57d
Source dataset
uspto-grants-1998_01
Patent number
US05705515

Reaction notes

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