Hydrochloric Acid → (2-Benzylthiazol-4-yl)methanol
Reaction equation
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13](OCC)=[O:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCOCC.O>C1(C)C=CC=CC=1>[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([CH2:13][OH:14])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
90 ml of a toluene solution of 2M/liter of diethyl sodium aluminum dihydride were added dropwise at -10° C. to a solution of 20 g of the product of Step A in 100 ml of toluene and the mixture was stirred at -5° C. for one hour. 150 ml of aqueous 2N hydrochloric acid were added dropwise to the mixture at -20° C. and then ether and water were added thereto. The mixture was filtered and the organic phase of the filtrate was washed with water, dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 7-3 methylene chloride-ethyl acetate mixture to obtain 13.6 g of (2-benzyl-4-thiazolyl)-methanol melting about 50° C.
Workup
- filtrationThe mixture was filtered
- washthe organic phase of the filtrate was washed with water
- customdried
- customevaporated to dryness
- customThe residue was chromatographed over silica gel
- washwas eluted with a 7-3 methylene chloride-ethyl acetate mixture
Sources & evidence
- ORD record
- ord-d91495a89de14125bee051b1489ed2b0
- Source dataset
- uspto-grants-1985_02
- Patent number
- US04501894
Reaction notes
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