Water → HCID 53842362, compound

HRID 1464767Notes

Reaction equation

HRID 1464767 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-a813eb11cf254ffa92ccf8ca0ebaff91
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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