2-(2-bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamide → 2-(2-Bromo-cyclopent-2-enyl)-ethanol

HRID 2422772Notes

Reaction equation

HRID 2422772 reaction equation
[Br:1][C:2]1[CH:3]([CH2:7][C:8](N(C)C)=[O:9])[CH2:4][CH2:5][CH:6]=1.C([BH-](CC)CC)C.[Li+]>C1COCC1>[Br:1][C:2]1[CH:3]([CH2:7][CH2:8][OH:9])[CH2:4][CH2:5][CH:6]=1

Participants

4

Reactant 2

HCID 219860692-(2-bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamideHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 219860942-(2-Bromo-cyclopent-2-enyl)-ethanolYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamide (Intermediate FOUR1) (1.93 g, 8.3 mmol) in THF (50 mL) was reacted with lithium triethylborohydride (19 mL, 1 M in THF) at 0° C. for 1 h. The mixture was treated with an aqueous work-up and the resultant alcohol was purified by column chromatography to give 0.92 g of 2-(2-bromo-cyclopent-2-enyl)-ethanol Intermediate FIVE1.

Workup

  1. additionThe mixture was treated with an aqueous work-up
  2. customthe resultant alcohol was purified by column chromatography

Sources & evidence

ORD record
ord-387b3983230b470497d3f96110edc889
Source dataset
uspto-grants-2011_06
Patent number
US07960423B2

Reaction notes

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