Trichloroacetyl chloride → HCID 89726833, compound

HRID 926353Notes

Reaction equation

HRID 926353 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][N:9]2[C:14]=1[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:5])[CH3:2].[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:17](=[O:18])[C:16]([Cl:21])([Cl:20])[Cl:15])[N:9]2[C:14]=1[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 12324173Ethyl 5,6,7,8-tetrahydroindolizine-1-carboxylate

Product 1

HCID 89726833HCID 89726833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid ethyl ester (Comp. No. 2b) (2 g, 10.3 mmol) in anhydrous dichloromethane (5 ml) was added trichloro-acetyl chloride (4.7 g, 25.9 mmol). The resulting mixture was stirred at room temperature for 3 days, and then evaporated to dryness. The crude product was purified by silica gel chromatography (eluting with 5 to 50% ethyl acetate in heptane) to give 2.74 g of 3-(2,2,2-trichloro-acetyl)-5,6,7,8-tetrahydro-indolizine-1-carboxylic acid ethyl ester. LC/MS (method 5): Rt=5.05 min; m/z=338.02 (M+H+).

Workup

  1. customevaporated to dryness
  2. customThe crude product was purified by silica gel chromatography (eluting with 5 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-100109e669f244e5aca250dcf0907608
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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