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

HRID 490684

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-9f2f750735574ac29f41f169be20f3aa
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528160B2

Linked notes

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