4-Thiazolecarboxylic acid, 2-propyl-, ethyl ester → 4-Thiazolemethanol, 2-propyl-

HRID 235088Notes

Reaction equation

HRID 235088 reaction equation
[CH2:1]([C:4]1[S:5][CH:6]=[C:7]([C:9](OCC)=[O:10])[N:8]=1)[CH2:2][CH3:3].[BH4-].[Na+]>C(O)C>[CH2:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][OH:10])[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 2036314-Thiazolecarboxylic acid, 2-propyl-, ethyl esterHCID 4311764Sodium borohydride

Product 1

HCID 184357644-Thiazolemethanol, 2-propyl-Yield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the compound from step 27c (1.2 g (6 mmol) and NaBH4 (490 mg, 13 mmol) in 15 mL of ethanol was stirred at reflux for 16 hours, then cooled and quenched with water. The mixture was extracted with ether, and the ether extract was washed with water and brine and dried over MgSO4. The solvent was removed under vacuum to give 0.72 g (76% yield) of the title compound. MS: 156(M+H)+, 173(M+NH4)30 . NMR (CDCl3) ,δ:7.04 (t, J=0.5 Hz, 1H), 4.74 (dd, J=0.5, 6 Hz, 2H), 2.96 (t, J=8 Hz, 2H), 2.70 (t, J=6 Hz, 1H), 1.82 (sx, J=8 Hz, 2H), 1.03 (t, J=8 Hz, 3H).

Workup

  1. temperatureat reflux for 16 hours
  2. temperaturecooled
  3. customquenched with water
  4. extractionThe mixture was extracted with ether
  5. extractionthe ether extract
  6. washwas washed with water and brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0f5db7e10c3540c0a9486e9d108c6a42
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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