Ethyl indole-2-carboxylate → HCID 53834851, compound

HRID 442880Notes

Reaction equation

HRID 442880 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].C(O[CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:20]1([CH:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 73125Ethyl indole-2-carboxylateHCID 274281Diphenylmethyl acetateHCID 516892Sodium Bicarbonate

Product 1

HCID 53834851HCID 53834851, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron trifluoride-ether complex (0.65 ml, 5.29 mmol) was added to a solution of ethyl indole-2-carboxylate (10.0 g, 52.9 mmol) in 100 ml of methylene chloride, and a solution of benzhydryl acetate (11.4 g, 50.2 mmol) in 50 ml of methylene chloride was dropwise added thereto, followed by stirring at room temperature for 40 minutes. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution for neutralization followed by extraction with chloroform. The resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to give a crude product. The obtained crude product was washed with diisopropyl ether to give 15.8 g (yield: 84%) of the title compound.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe resulting organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a crude product
  6. customThe obtained crude product
  7. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-c0f870c3b0ee4fa9bf7e15304b0767ed
Source dataset
uspto-grants-1999_04
Patent number
US05891902

Reaction notes

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