Ethyl 5-phenylthiazole-4-carboxylate → HCID 59455496, compound

HRID 915684Notes

Reaction equation

HRID 915684 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[C:11]1([C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH2:4][OH:3])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 12300673Ethyl 5-phenylthiazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 59455496HCID 59455496, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepare a cold (0° C.) solution of 5-phenylthiazole-4-carboxylic acid ethyl ester (3.0 g, 12.9 mmol) in tetrahydrofuran (150 mL). Add LiAlH4 (488 mg, 12.9 mmol). Allow the reaction to slowly warm to room temperature and stir for 3 hours. Quench with water (25 mL) and filter through Celite®. Concentrate the filtrate in vacuo to a residue. Chromatograph (silica gel, 3:7 hexane/ethyl acetate) to afford (5-phenylthiazol-4-yl)methanol (1.4 g). 1H NMR (CDCl3) δ 8.75 (s, 1H), 7.40-7.55 (m, 5H), 4.80 (d, J=4 Hz, 2H), 3.15-3.22 (m, 1H).

Workup

  1. customthe reaction
  2. customQuench with water (25 mL)
  3. filtrationfilter through Celite®
  4. concentrationConcentrate the filtrate in vacuo to a residue

Sources & evidence

ORD record
ord-c91c0682e7784c08987edb7521b6a972
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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