Hydrochloric Acid → HCID 22627242, compound

HRID 1108734Notes

Reaction equation

[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[C:7]([CH:18]=[O:19])=[C:6]1[CH2:20][CH2:21][CH3:22].CC(=CC)C.[Na].Cl([O-])=[O:34].[Na+].Cl>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[C:7]([C:18]([OH:34])=[O:19])=[C:6]1[CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of methyl 1-(2-chlorobenzyl)-3-formyl-2-propylindole-6-carboxylate (263 mg), 2-methyl-2-butene (220 mg) and sodium dihydrogenohosphate (128 mg) in a mixture of tert-butanol (7 ml) and water (1.3 ml) was added sodium chlorite (219 mg) at 20° C. The reaction mixture was stirred at 40° C. for 2 hours. The reaction mixture was acidified with 1N hydrochloric acid at 0° C. and extracted with chloroform three times. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2) to give 1-(2-chlorobenzyl)-6-methoxycarbonyl-2-propylindole-3-carboxylic acid (94 mg) as pale yellow crystals.

Workup

extractionextracted with chloroform three times
dry with materialThe organic phase was dried over sodium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2)

Sources & evidence

ORD record: ord-4a146cec59534b1a9848463b34b0b40a
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069156

Reaction notes

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