Water → 5-[2-(2-chlorophenyl)ethyl]-3,4-dihydro-2H-pyrrole

HRID 81389

Reaction equation

HRID 81389 reaction equation
C[N:2]1[CH2:6][CH2:5][CH:4]=[CH:3]1.[Li][CH2:8]CCC.[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br.O>C1COCC1>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][CH2:8][C:3]1[CH2:4][CH2:5][CH2:6][N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11905alpha-Bromo-o-chlorotolueneHCID 5574631H-Pyrrole, 2,3-dihydro-1-methyl-HCID 178418339Butyllithium

Product 1

HCID 584839715-[2-(2-chlorophenyl)ethyl]-3,4-dihydro-2H-pyrrole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.1 3 ml of 1-methylpyrroline are dissolved in 25 nil of THF and deprotonated at −78° C. for 30 minutes using 22.6 ml of BuLi (1 M in hexane). 6.5 g of 2-chlorobenzyl bromide are dissolved in 25 ml of THF and added dropwise at the temperature indicated. After 30 minutes, the mixture is allowed to warm to RT for 12 hours. For work-up, 50 ml of water are added, and the mixture is extracted to exhaustion with dichloromethane. The combined organic phases are dried over sodium sulfate, evaporated and purified by chromatography on silica gel, giving 4.5 g of 5-[2-(2-chlorophenyl)ethyl]-3,4-dihydro-2H-pyrrole as a colourless oil, which is employed in the next reaction; Rt.: 1.303 min; [M+H]+208.

Workup

  1. additionadded dropwise at the temperature
  2. waitAfter 30 minutes
  3. extractionthe mixture is extracted to exhaustion with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customevaporated
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-c9f5f5ea06f24b79bc37081c1a132fe8
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Linked notes

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