Oxalyl chloride → Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

HRID 37828Notes

Reaction equation

HRID 37828 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].[C:7]1([C:13]2[CH:14]=[C:15]3[N:20]([CH:21]=2)[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.C1COCC1>[O:3]=[C:2]([C:21]1[N:20]2[C:15]([CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:14][C:13]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]([Cl:6])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 150316492-Phenyl-5,6,7,8-tetrahydroindolizine

Product 1

HCID 86649692Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chlorideYield 91.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (17.2 mL, 0.19 mol) was added to an ice-cold solution of 2-phenyl-5,6,7,8-tetrahydro-indolizine (32 g, 0.16 mol) in a mixture of toluene (20 mL) and THF (30 mL). The reaction mixture was allowed to warm to room temperature and stirred for 30 min. then concentrated under vacuum. The residue was triturated with petrol (5×300 mL) to afford oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (42 g, 89%) as a dark yellow solid.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue was triturated with petrol (5×300 mL)

Sources & evidence

ORD record
ord-07ea9e649745445f9fdc5bfad9c4e80f
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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