Benzene → HCID 86739249, compound

HRID 1388278Notes

Reaction equation

HRID 1388278 reaction equation
[CH3:1][C:2]1([CH3:12])[C@@H:4](/[CH:5]=[CH:6]\[C:7]#[N:8])[C@H:3]1[C:9](Cl)=[O:10].[CH3:13][OH:14].C1C=CC=CC=1.N1C=CC=CC=1>O>[CH3:1][C:2]1([CH3:12])[C@@H:4](/[CH:5]=[CH:6]\[C:7]#[N:8])[C@H:3]1[C:9]([O:14][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 1049PyridineHCID 131713385HCID 131713385, compound

Product 1

HCID 86739249HCID 86739249, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

1.85 g of (1R,cis) 2,2-dimethyl-3-[(Z)-cyanoethenyl]-cyclopropane-1-carboxylic acid chloride were added at 0° to solution of 2 ml of methanol, 10 ml of benzene and 1 ml of pyridine and the reaction solution was stirred at 20° C. for 16 hours and was poured into water. The mixture was extracted with benzene and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with benzene to obtain 0.511 g of methyl (1R,cis) 2,2-dimethyl-3[(Z)-2-cyanoethenyl]cyclopropane-1-carboxylate.

Workup

  1. extractionThe mixture was extracted with benzene
  2. customthe organic phase was dried
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washeluted with benzene

Sources & evidence

ORD record
ord-da0f16fe58684ffc8b7040f51683b930
Source dataset
uspto-grants-1984_02
Patent number
US04431576

Reaction notes

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