Ammonium Chloride → HCID 86739096, compound

HRID 648236Notes

Reaction equation

HRID 648236 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5](=[C:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:6]#[N:7])[CH3:2].[CH3:14][O:15][C:16]1C=[CH:23][CH:22]=[CH:21][C:17]=1C[Mg]Cl.[Cl-].[NH4+]>O1CCCC1>[C:6]([CH:5]([CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1)[C:4]1[CH:23]=[CH:22][CH:21]=[CH:17][C:16]=1[O:15][CH3:14])#[N:7].[CH2:1]([O:3][C:4](=[O:13])[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 223257Ethyl 2-cyano-2-cyclopentylideneacetateHCID 178489472HCID 178489472, compound

Product 1

HCID 86739096HCID 86739096, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 39.9 g cyclopentylidene cyanoacetic acid ethyl ester in 350 ml tetrahydrofuran is added dropwise to a solution of 2-methoxybenzyl magnesium chloride (produced from 5.3 g magnesium and 31.2 g 2-methoxybenzyl chloride in 400 ml ether). The mixture is stirred for 2 hours at room temperature. The mixture is treated with a 300 ml 15% ammonium chloride solution. The product is extracted with ether and the ethereal solution concentrated to yield crude α-cyano-[1-(2-methoxybenzyl)cyclopentane]-acetic acid ethyl ester which distilled at 140°-180°/0.002 mm Hg.

Workup

  1. extractionThe product is extracted with ether
  2. concentrationthe ethereal solution concentrated

Sources & evidence

ORD record
ord-5b56a91cccf2463fb581b5f3881600ca
Source dataset
uspto-grants-1983_10
Patent number
US04411913

Reaction notes

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