Benzyl chloroformate → Benzyl 3-acetyl-1H-indole-1-carboxylate

HRID 1381024Notes

Reaction equation

HRID 1381024 reaction equation
[H-].[Na+].[C:3]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH3:4].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1>[C:16]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:3](=[O:5])[CH3:4])=[CH:7]1)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 128023-AcetylindoleHCID 24758Sodium hydride

Product 1

HCID 13711099Benzyl 3-acetyl-1H-indole-1-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of sodium hydride (3.77 g, 50% in oil, 7.86 mmol, extracted with hexanes) in THF (30 ml) at 0° C. under nitrogen was added dropwise 3-acetyl indole (10.0 g, 62.9 mmol) in THF (15 ml). After warming to room temperature and stirring one hour, the mixture was cooled to 0° C. and benzyl chloroformate (8.97 ml, 62.9 mmol) was added dropwise. The reaction was allowed to warm to room temperature and stir overnight. The excess sodium hydride was destroyed at 0° C. with 40 ml H2O. The mixture was then extracted three times with CHCl3 (total volume 120 ml), dried with MgSO4, filtered and evaporated to an off-white solid. Recrystallization from hexanes afforded 15.85 g (86%) of product: mp 112°-113°; Anal. Calcd for C18H15NO3 : C, 73.79; H, 5.16; N, 4.78. Found: C, 73.86; H, 5.29; N, 4.95.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstir overnight
  4. customThe excess sodium hydride was destroyed at 0° C. with 40 ml H2O
  5. extractionThe mixture was then extracted three times with CHCl3 (total volume 120 ml)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customevaporated to an off-white solid
  9. customRecrystallization from hexanes

Sources & evidence

ORD record
ord-7f5b88b51385424e949b9c9ba9cdba82
Source dataset
uspto-grants-1986_04
Patent number
US04584385

Reaction notes

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