Water → HCID 53842362, compound

HRID 1756160Notes

Reaction equation

HRID 1756160 reaction equation
[S:1]1[C:5]([CH:6]=[CH:7][C:8](OC)=[O:9])=[CH:4][N:3]=[CH:2]1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C(OCC)(=O)C>[S:1]1[C:5]([CH:6]=[CH:7][CH2:8][OH:9])=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 54234703HCID 54234703, compound

Product 1

HCID 53842362HCID 53842362, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

700 mg of methyl β-(5-thiazolyl)acrylate [see Chem. Pharm. Bull., 35 823 (1987)] was dissolved in 10 ml of tetrahydrofuran, and under a nitrogen atmosphere, 8.1 ml of a 1M toluene solution of diisobutylaluminum hydride was added dropwise at -70° C. The mixture was stirred at this temperature for 50 minutes, and water and ethyl acetate were added to the solution. The precipitate was removed by filtration, and the filtrate was worked up in a customary manner to give 279 mg of 3-(5-thiazolyl)-2-propen-1-ol as a yellow oil.

Workup

  1. customThe precipitate was removed by filtration

Sources & evidence

ORD record
ord-34c6074798144379b6918c156f179d2e
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

Loading…