Hydrochloric Acid → 2-{2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}ethanol

HRID 11039

Reaction equation

HRID 11039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2.[O:21]1CCC[CH2:23][CH:22]1OCCBr.Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[N:11]([CH2:23][CH2:22][OH:21])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([O:19][CH3:20])=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 695838012-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indole

Product 1

HCID 738577322-{2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}ethanolYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Alkylation of 2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indole (27) prepared according to example 37 with 2-bromoethyl tetrahydro-2H-pyran-2-yl ether using the procedure described in example 38 followed by reaction of the crude product with 2N HCl in methanol gave 2-{2-[2-(2-Chlorophenyl)ethenyl]-5-methoxy-1H-indol-1-yl}ethanol (III; Ar=2-chlorophenyl, R10═CH2CH2OH) (44) in a yield of 86% as a mixture of E/Z isomers, which was used without further purification.

Sources & evidence

ORD record
ord-edee55bf520b4f37adbc078a7c1a78ec
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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