1,1-Dimethoxyethyl(dimethyl)amine → 2-(2-bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamide

HRID 28730

Reaction equation

HRID 28730 reaction equation
[Br:1][C:2]1[CH:3](O)[CH2:4][CH2:5][CH:6]=1.C[O:9][C:10](OC)([N:12]([CH3:14])[CH3:13])[CH3:11]>C1(C)C=CC=C(C)C=1>[Br:1][C:2]1[CH:3]([CH2:11][C:10]([N:12]([CH3:14])[CH3:13])=[O:9])[CH2:4][CH2:5][CH:6]=1

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 111374622-Bromo-cyclopent-2-enol2×

Product 1

HCID 219860692-(2-bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamideYield 63%

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

2-Bromo-cyclopent-2-enol (Intermediate D3) (2.18 g, 13.4 mmol) and N,N-dimethylacetamide dimethylacetal (3.5 mL, 21.5 mmol) in m-xylene (˜20 mL) were heated to 140° C. for 14 h. The mixture was freed of solvent and the residue was purified on a column of silica gel with 30% to 50% EtOAc:hexanes to give 2-(2-bromo-cyclopent-2-enyl)-N,N-dimethyl-acetamide (Intermediate FOUR1) 1.95 g (63%) as a brown oil.

Workup

  1. customthe residue was purified on a column of silica gel with 30% to 50% EtOAc

Sources & evidence

ORD record
ord-c73515496a554d98b9072082e3c055ec
Source dataset
uspto-grants-2008_09
Patent number
US07419994B2

Linked notes

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