Oxalyl chloride → (6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester

HRID 490760

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.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[CH3:24][O-:25].[Na+]>CCOCC>[CH3:24][O:25][C:18](=[O:22])[C:19]([C:13]1[C:12]2[C:16](=[CH:17][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[NH:15][CH:14]=1)=[O:20]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 6-benzoxyindole (1.05 g, 4.7 mmol) in ether (8 mL) is added oxalyl chloride (0.45 mL) at 0˜5° C., stirred for 2 hrs. The reaction mixture is cooled to −78° C., sodium methoxide (25% w/w in methanol, 2.4 mL) is added, warmed up to room temperature, quenched by water. Solid product is collected by filtration, washed by water and dried under vacuum.

Workup

temperaturewarmed up to room temperature
customquenched by water
filtrationSolid product is collected by filtration
washwashed by water
customdried under vacuum

Sources & evidence

ORD record: ord-f97a990fb24c4b1b9c321f775e1f21f9
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528160B2

Linked notes

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