Sodium hydride → HCID 9797925, compound

HRID 1596532Notes

Reaction equation

HRID 1596532 reaction equation
[H-].[Na+].[N:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]2=[CH:13][CH:14]=[CH:15][C:4]=12.[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20]Br>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:20][N:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]2[CH2:13][CH2:14][CH2:15][C:4]1=2

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 6397264-(Bromomethyl)-1,2-dichlorobenzeneHCID 21702189HCID 21702189, compound

Product 1

HCID 9797925HCID 9797925, compoundYield 83%

Procedure

Sodium hydride (25 mg, 60%), was added to a solution of ethyl cyclopenta[b]pyrrole-2-carboxylate (96 mg) (T. Aubert et al., J. Chem. Soc. Perkin Trans. 1, 1989, 1369) and the reaction stirred for 30 minutes. 3,4-Dichlorobenzyl bromide (154 mg) was added and stirring continued for a further 2 hours. The reaction was quenched by addition of water and extracted with ether. Combined organic extracts were dried (MgSO4) and concentrated and the residue purified by column chromatography using isohexane-5% ethyl acetate as eluent to give the product as a white crystalline solid (0.15 g, 83%), NMR d(DMSO) 1.18 (3H, t), 2.30 (1H, m), 2.53 (2H, m), 4.10 (2H, q), 5.40 (2H, s), 6.67 (1H, s), 6.92 (1H, dd), 7.25 (1H, s), 7.57 (1H, d); M/z (+) 338 (M+).

Workup

  1. stirringstirring
  2. waitcontinued for a further 2 hours
  3. customThe reaction was quenched by addition of water
  4. extractionextracted with ether
  5. dry with materialCombined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-3bd97c986276493ab7923dfa9f459bcd
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Reaction notes

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