Benzene → HCID 54262875, compound

HRID 223760Notes

Reaction equation

HRID 223760 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:4]([CH:5]=[C:6]2[CH2:10][CH2:9]O[C:7]2=O)[CH:3]1[C:12](Cl)=[O:13].[OH:16][C@H:17]1[CH2:21][C:20](=[CH2:22])[C:19]([CH2:23][CH:24]=[CH2:25])=[C:18]1[CH3:26].O.[CH:28]1C=CC=CC=1>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[C@@H:4]([CH:5]=[C:6]2[CH2:10][CH2:9][CH2:28][CH2:7]2)[C@H:3]1[C:12]([O:16][CH:17]1[CH2:21][C:20](=[CH2:22])[C:19]([CH2:23][CH:24]=[CH2:25])=[C:18]1[CH3:26])=[O:13]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 962WaterHCID 22818710HCID 22818710, compoundHCID 54401562HCID 54401562, compound

Product 1

HCID 54262875HCID 54262875, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 5.4 g of (1R, trans) 2,2-dimethyl-3-(2-oxo-3-tetrahydrofuranylidenemethyl)-cyclopropane-1-carboxylic acid chloride in 50 ml of benzene was added at less than 25° C. over 15 minutes to a suspension of 3 g of (1S)-hydroxy-2-methyl-3-allyl-4-methylene-cyclopent-2-ene in 10 ml of benzene and 3 ml of pyridine at 20° C. and the mixture was stirred at 20° C. for 20 hours. 30 ml of water were added and the mixture was stirred for 15 minutes. The decanted aqueous phase was extracted with benzene and 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 7-3 cyclohexane-ethyl acetate mixture containing 1‰ triethylamine yielded 2.61 g of (1S) 2-methyl-3-allyl-4-methylene-cyclopent-2-ene-1-yl (1R, trans) 2,2-dimethyl-3-(2-oxo-3-tetrahydrofuranylidenemethyl)-cyclopropane-1-carboxylate with a specific rotation of [α]D20 =-28.5°±2.5° (c=0.5% in ethanol).

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. extractionThe decanted aqueous phase was extracted with benzene
  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 7-3 cyclohexane-ethyl acetate mixture
  9. additioncontaining 1‰ triethylamine

Sources & evidence

ORD record
ord-e30811ee367e4d3bb587f17cb3ab0b79
Source dataset
uspto-grants-1982_10
Patent number
US04356187

Reaction notes

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