Sodium borohydride → 3-(4-Phenylthiazol-2-yl)propan-1-ol

HRID 1397333Notes

Reaction equation

HRID 1397333 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][C:14](OCC)=[O:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][OH:15])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67325597Ethyl 3-(4-phenylthiazol-2-yl)propanoate

Product 1

HCID 673252893-(4-Phenylthiazol-2-yl)propan-1-olYield 95.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of ethyl 3-(4-phenylthiazol-2-yl)propanoate (0.5 g, 1.91 mmol) in MeOH—H2O (10 mL, 9:1 v/v) was cooled to 0° C. and sodium borohydride (0.29 g, 7.65 mmol) was added. The reaction mixture was warmed to room temperature and further stirred for 8 h. The mixture was quenched with ice water and the organic product was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 3-(4-phenylthiazol-2-yl)propan-1-ol (0.4 g, yield 95%) as colorless liquid, which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 7.87-7.85 (m, 2H), 7.44-7.40 (m, 2H), 7.35-7.32 (m, 2H), 3.83-3.81 (t, J=5.8 Hz, 2H), 3.24-3.21 (m, 3H), 2.14-2.08 (m, 2H). MS (ESI) m/z: Calculated for C12H13NOS: 219.07. found: 220.2 (M+H)+.

Workup

  1. customThe mixture was quenched with ice water
  2. extractionthe organic product was extracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31d38c58a21a409e9e1965dcee674119
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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