Benzene → 3-(Dimethoxymethyl)hept-2-en-4-yne

HRID 371974Notes

Reaction equation

HRID 371974 reaction equation
[CH:1]1C=CC=C[CH:2]=1.C([Li])CCC.[CH3:12][O:13][CH:14]([O:21][CH3:22])[C:15](=O)[C:16]#[C:17][CH2:18][CH3:19]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CCCCCC>[CH3:12][O:13][CH:14]([O:21][CH3:22])[C:15](=[CH:1][CH3:2])[C:16]#[C:17][CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 241BenzeneHCID 203140171,1-Dimethoxyhex-3-yn-2-oneHCID 178418339Butyllithium

Product 1

HCID 714414643-(Dimethoxymethyl)hept-2-en-4-yne

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8058HexaneSolvent

Procedure

Ethyltriphenylphosphonium bromide (24.8 g) is stirred with 100 ml benzene, and 40 ml (1.6 N) butyl lithium in hexane is added over about one-half hour with a water bath used to take up the slight heat of reaction. The mixture (bright orange) is stirred at room temperature for 0.75 hour, and 10.0 g of the 1,1-dimethoxy-3-hexyne-2-one is added dropwise in one-half hour.

Workup

  1. additionis added over about one-half hour with a water bath
  2. temperatureslight heat of reaction

Sources & evidence

ORD record
ord-ea94bc1411954d31a2eb20d4ace01460
Source dataset
uspto-grants-1978_05
Patent number
US04088696

Reaction notes

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