Propylene Oxide → (6-Benzyloxy-indol-1-yl)-propan-2-ol

HRID 890893

Reaction equation

HRID 890893 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]1[O:21][CH:19]1[CH3:20]>>[OH:21][CH:19]([CH3:20])[CH2:18][N:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:17]=2)[CH:13]=[CH:14]1

Participants

3

Reactant 2

HCID 6378Propylene OxideHCID 2608046-(benzyloxy)-1H-indole

Product 1

HCID 22247173(6-Benzyloxy-indol-1-yl)-propan-2-ol

Procedure

6-Benzyloxyindole (1) (Batcho and Leimgruber, Organic Syntheses, Collective Vol. 7, p. 34 (1990)) is reacted with (±)-propylene oxide and a base in an organic solvent to yield (±)-1-(2-hydroxypropyl)-6-benzyloxyindole (2). Preferably the base is sodium hydride and the solvent is tetrahydrofuran. The temperature is 0° C. to 25° C., preferably about 10° C. Preferably an inert atmosphere, e.g., nitrogen or argon, is maintained.

Sources & evidence

ORD record
ord-c9269fc643d04eaf8aacfbc51d040769
Source dataset
uspto-grants-2006_02
Patent number
US06998489B2

Linked notes

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