Sodium borohydride → 2-(Thiazol-2-ylmethoxy)ethanol

HRID 1096820Notes

Reaction equation

HRID 1096820 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][CH2:6][C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[BH4-].[Na+]>CO>[S:8]1[CH:9]=[CH:10][N:11]=[C:7]1[CH2:6][O:5][CH2:4][CH2:3][OH:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66783731HCID 66783731, compound

Product 1

HCID 451216842-(Thiazol-2-ylmethoxy)ethanolYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A cooled (0° C.) sol. of (thiazol-2-ylmethoxy)acetic acid methyl ester (31.0 g, 165.6 mmol) in MeOH (830 mL) was treated portionwise with NaBH4 (31.0 g, 1.66 mol). The reaction mixture was allowed to warm to rt over 1 h. The mixture was then quenched with water, and extracted with CH2Cl2 (3×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil (22.9 g, 87%) that was not further purified. LC-MS: tR=0.44 min, ES+: 160.19.

Workup

  1. customThe mixture was then quenched with water
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materiallayers were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e6118091d65542f7b97b4240cc204a09
Source dataset
uspto-grants-2012_03
Patent number
US08138340B2

Reaction notes

Loading…