Water → HCID 20138923, compound

HRID 280174Notes

Reaction equation

HRID 280174 reaction equation
[C:1]([CH:3]1[C:6]2=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]2[CH2:4]1)#[N:2].[H-].[Na+].[CH3:15]I.O>C1COCC1.C(OCC)C>[C:1]([C:3]1([CH3:15])[C:6]2=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=[C:5]2[CH2:4]1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12238660Bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile, 4-methoxy-

Product 1

HCID 20138923HCID 20138923, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-cyano-5-methoxybenzocyclobutene (47.3 ml) in THF (300 ml) is added dropwise to a stirred suspension of NaH (23.8 g, 60% in mineral oil) and methyl iodide (37 ml) in THF (300 ml) under nitrogen and the reaction mixture is stirred at RT for three hours. H2O is added to the reaction mixture which is diluted with diethyl ether, washed with water, 10% aq. sodium sulphite, sat'd sodium chloride, dried, filtered and the filtrate evaporated in vacuo affording the desired product as a yellow oil.

Workup

  1. washwashed with water, 10% aq. sodium sulphite
  2. customdried
  3. filtrationfiltered
  4. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-60f1b763ab9a4b0987c758201c9e6331
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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