Benzene → HCID 54341468, compound

HRID 223765Notes

Reaction equation

HRID 223765 reaction equation
[N:1]1C=CC=C[CH:2]=1.[CH3:7][C:8]1([CH3:20])[CH:10](/[CH:11]=[CH:12]/[C:13](OC)=O)[CH:9]1[C:17](O)=O.[CH:21]1C=CC=CC=1.Cl>O>[CH3:21][C:9]1[CH2:17][CH2:20][C:8](=[CH:7][C:2]#[N:1])[C:10]=1[CH2:11][CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 1049PyridineHCID 12807747HCID 12807747, compound

Product 1

HCID 54341468HCID 54341468, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 ml of pyridine were added at 5° C. to a mixture of 3 g of the product of Step A, 3 g of (1R, trans) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-carboxylic acid chloride and 50 ml of benzene and the mixture was held at 5° C. for 15 minutes, at 20° C. for 2 hours and was then poured into a mixture of 18 ml of 2 N hydrochloric acid and 100 ml of water at 5° C. The mixture was extracted with ether and the organic phase was washed with water, dried and evaporated to dryness. The 6.5 g of residue was chromatographed over silica gel and was eluted with a 97-3 toluene-ethyl acetate mixture to obtain 4.93 g of (1S) 2-methyl-3-allyl-4-cyanomethylene-cyclopent-2-ene-1-yl (1R, trans) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α ]D20 =-162.5°±3.5° (c=0.6% in benzene).

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe 6.5 g of residue was chromatographed over silica gel
  6. washwas eluted with a 97-3 toluene-ethyl acetate mixture

Sources & evidence

ORD record
ord-e569d76391754e77bda60f69eb3fb687
Source dataset
uspto-grants-1982_10
Patent number
US04356187

Reaction notes

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