Benzene → HCID 54262875, compound

HRID 223758Notes

Reaction equation

HRID 223758 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:7][C:8]1([CH3:20])[CH:10]([CH:11]=[C:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:9]1[C:17](Cl)=[O:18].N1C=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH2:27]>>[CH3:7][C:8]1([CH3:20])[C@@H:10]([CH:11]=[C:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C@H:9]1[C:17]([O:27][CH:22]1[CH2:23][C:24](=[CH2:25])[C:4]([CH2:5][CH:6]=[CH2:1])=[C:3]1[CH3:2])=[O:18]

Participants

5

Reactant 4

HCID 241Benzene2×HCID 962WaterHCID 1049PyridineHCID 12952596HCID 12952596, compound

Product 1

HCID 54262875HCID 54262875, compound

Conditions

Temperature
20 °C

Procedure

30 ml of a benzene solution of (1R, cis) 2,2-dimethyl-3-cyclopentylidenemethyl-cyclopropane-1-carboxylic acid chloride prepared from 7 g of the corresponding acid were added at 20° C. over 15 minutes to a mixture of 4 g of 1S-hydroxy-2-methyl-3-allyl-4-methylene-cyclopent-2-ene, 10 ml of benzene and 5 ml of pyridine and the mixture was stirred at 20° C. for 20 hours and was then poured into 30 ml of water. The mixture was stirred for 10 minutes and was then extracted with methylene chloride. The combined organic phases were washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 95-5 cyclohexane-ethyl acetate mixture containing 1‰ triethylamine yielded 4.1 g of (1S) 2-methyl-3-allyl-4-methylene-cyclopent-2-ene-1-yl (1R, cis) 2,2-dimethyl-3-cyclopentylidenemethyl-cyclopropane-1-carboxylate.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionwas then extracted with methylene chloride
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customthe residue was chromatographed over silica gel
  8. washElution with a 95-5 cyclohexane-ethyl acetate mixture
  9. additioncontaining 1‰ triethylamine

Sources & evidence

ORD record
ord-70493b9f7c1f49eea7658a54c1f0719e
Source dataset
uspto-grants-1982_10
Patent number
US04356187

Reaction notes

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