Methyl formate → HCID 67776698, compound

HRID 705947Notes

Reaction equation

HRID 705947 reaction equation
C[C:2](C)([O-:4])C.[K+].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].C(OC)=O>C1COCC1>[OH:4][CH:2]=[C:18]([CH2:17][C:9]1[N:8]([CH3:7])[C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 23559703HCID 23559703, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67776698HCID 67776698, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium tert-butoxide (300 mg, 2.67 mmol) in dry THF (5 mL) were added dropwise a solution of methyl 3-(1-methyl-1H-indol-2-yl)propanoate (322 mg, 1.482 mmol) and methyl formate (0.30 mL, 4.87 mmol) in dry THF (5 mL) over 15 min. The mixture was stirred at room temperature for 1 h. Concentration in vacuo then afforded the title compound (400 mg, 0.522 mmol, 35.2% yield). LCMS: rt=2.82 min, [M+H+]=246

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ded04bc7bcac497a8e84676046709a3b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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