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

HRID 1249232Notes

Reaction equation

HRID 1249232 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

6

Reactant 4

HCID 962WaterHCID 10256Indole-3-CarboxaldehydeHCID 10387Benzyl chloroformateHCID 24758Sodium hydride

Product 1

HCID 13711097Benzyl 3-formyl-1H-indole-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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°

Workup

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

Sources & evidence

ORD record
ord-c5f5c7f62e084d32b44e8b1dc6485aaf
Source dataset
uspto-grants-1986_12
Patent number
US04629794

Reaction notes

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