Benzene → HCID 54262875, compound

HRID 223759Notes

Reaction equation

HRID 223759 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:4]([CH:5]=[C:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:3]1[C:11](Cl)=[O:12].[OH2:15].[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[C@@H:4]([CH:5]=[C:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)[C@H:3]1[C:11]([O:15][CH:4]1[CH2:3][C:2](=[CH2:1])[C:19]([CH2:20][CH:21]=[CH2:16])=[C:18]1[CH3:17])=[O:12]

Participants

5

Reactant 3

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

Product 1

HCID 54262875HCID 54262875, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 7.08 g of (1R, trans) 2,2-dimethyl-3-cyclopentylidenemethyl-cyclopropane-1-carboxylic acid chloride in 3 ml of benzene was added over 10 minutes at 28° C. to a suspension of 5 g of 1S-hydroxy-2-methyl-3-allyl-4-methylene-cyclopent-2-ene in 15 ml of benzene and 2.96 ml of pyridine and the mixture was stirred at 20° C. for 17 hours. 20 ml of water were added to the mixture which was stirred for 10 minutes and the decanted aqueous phase was extracted with benzene. The combined organic phases were washed with water and the wash waters were extracted with benzene. The combined organic phases were dried over magnesium sulfate and were filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 95-5 cyclohexane-ethyl acetate mixture containing 1‰ triethylamine to obtain 8.24 g of (1S) 2-methyl-3-allyl-4-methylene-cyclopent-2-ene-1-yl (1R, trans) 2,2-dimethyl-3-cyclopentylidienemethyl-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =-87°±1° (c=0.9% in ethanol).

Workup

  1. stirringwas stirred for 10 minutes
  2. extractionthe decanted aqueous phase was extracted with benzene
  3. washThe combined organic phases were washed with water
  4. extractionthe wash waters were extracted with benzene
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationwere filtered
  7. customthe filtrate was evaporated to dryness under reduced pressure
  8. customThe residue was chromatographed over silica gel
  9. washwas eluted with a 95-5 cyclohexane-ethyl acetate mixture
  10. additioncontaining 1‰ triethylamine

Sources & evidence

ORD record
ord-e88935b2b407430686d7e83a8d6bac11
Source dataset
uspto-grants-1982_10
Patent number
US04356187

Reaction notes

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