Water → Benzyl 3-formyl-1H-indole-1-carboxylate

HRID 1381022Notes

Reaction equation

[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].O>C1COCC1>[C:15]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH:12]=[O:13])=[CH:4]1)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium hydride (1.99 g, 50% in oil, 41.4 mmol, extracted with hexanes) was stirred in THF (50 ml) in a flame-dried flask at 0° C. under nitrogen. Indole-3-carboxaldehyde (5.00 g, 34.5 mmol) was added as a powder in small portions, and then the mixture was warmed to 40° C. for 30 min. The mixture was again cooled to 0° C., and benzyl chloroformate (4.92 ml, 34.5 mmol) was added. After warming to room temperature and stirring overnight, the mixture was poured into water (50 ml) and extracted with CH2Cl2 (50 ml). The organic layer was washed with water (50 ml), dried with MgSO4, filtered and evaporated to 9.2 g (95%) of a gold-brown oil. Crystallization from hot hexane gave 8.47 g (88%) of white crystalline product: mp 70°-71° Anal. Calcd for C17H13NO3 : C, 73.19; H, 4.70; N, 5.02. Found: C, 72.79; H, 5.16; N, 5.24.

Workup

temperatureThe mixture was again cooled to 0° C.
temperatureAfter warming to room temperature
extractionextracted with CH2Cl2 (50 ml)
washThe organic layer was washed with water (50 ml)
dry with materialdried with MgSO4
filtrationfiltered
customevaporated to 9.2 g (95%) of a gold-brown oil
customCrystallization from hot hexane

Sources & evidence

ORD record: ord-e5fc7d7f924e40358935e7fe84b0a06c
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04584385

Reaction notes

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