Ethyl chloroformate → Ethyl 2,3-dihydro-7-(2-propen-1-yl)-1H-indole-1-carboxylate

HRID 979818Notes

Reaction equation

HRID 979818 reaction equation
[CH2:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH2:10][CH2:9]2)[CH:2]=[CH2:3].Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>N1C=CC=CC=1>[CH2:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 15723560HCID 15723560, compound

Product 1

HCID 86741185Ethyl 2,3-dihydro-7-(2-propen-1-yl)-1H-indole-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The product from Example 113 (0.8 g) was dissolved in pyridine (3 ml), cooled to 0° C. and ethyl chloroformate (0.77 ml) was added. After 10 minutes, the reaction was quenched with water and extracted with diethylether. The organic layer was separated and washed with cold 2% hydrochloric acid, 5% sodium bicarbonate, brine and dried. The solvent was evaporated in vacuo affording the desired compound in 90% yield as an oil.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with diethylether
  3. customThe organic layer was separated
  4. washwashed with cold 2% hydrochloric acid, 5% sodium bicarbonate, brine
  5. customdried
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7aa44ffbd6e444d888dba45bf27ad28c
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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