Methyl formate → Methyl(2Z)-3-hydroxy-2-(1H-indol-1-ylmethyl)-2-propenoate

HRID 705941Notes

Reaction equation

HRID 705941 reaction equation
CC(C)([O-])C.[K+].[CH:7]([O:9][CH3:10])=[O:8].[N:11]1([CH2:20][CH2:21][C:22](OC)=[O:23])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1>C1COCC1>[OH:23]/[CH:22]=[C:21](/[CH2:20][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)\[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 5150745Methyl 3-(1H-indol-1-yl)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67953507Methyl(2Z)-3-hydroxy-2-(1H-indol-1-ylmethyl)-2-propenoateYield 114.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the suspension of potassium tert-butoxide (1.0 g, 8.91 mmol) in dry THF (10 mL) was added dropwise solution of methyl formate (1.0 ml, 16.22 mmol) and methyl 3-(1H-indol-1-yl)propanoate (1.0 g, 4.92 mmol) in dry THF over 30 min. The mixture was stirred at room temperature for 1 h. Concentration in vacuo then afforded the crude title compound (1.3 g). LCMS: rt=2.59 min, [M+H]=232

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-b0851d85e10642739cce15e84d41087c
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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