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Ethyl Acetate → 3-Hydroxyacetyl-6-(benzyloxy)indole

HRID 1607608
Notes
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Reaction equation

HRID 1607608 reaction equation
Cl[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].C(N)=[O:23].O.CCOC(C)=O>O1CCOCC1>[OH:23][CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 109026373-Chloroacetyl-6-(benzyloxy)indoleHCID 13001166Formamide--water (1/1)

Product 1

HCID 141683013-Hydroxyacetyl-6-(benzyloxy)indoleYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 11 in dioxane was added to formamide-water (10:1). The mixture was stirred at 110° C. for 10 hrs., then worked up and purified as described above to yield 82% of 13 as colorless prisms with mp 194°-195° C. (EtOAc).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-e6c7b58cdebc4ee5bf79639f88691b22
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04866084

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes