Benzene → 2-methyl-4-oxo-3-(2propenyl)-2-cyclopenten-1-yl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylate

HRID 1639428Notes

Reaction equation

HRID 1639428 reaction equation
[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:3]1[C:17](Cl)=[O:18].CC1(C)[C@@H](/C=C\C(OCC(F)(F)F)=O)[C@H]1C([O:37][C@H:38]([C:52]#N)[C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([O:45]C2C=CC=CC=2)[CH:40]=1)=O.[CH:55]1C=CC=CC=1.Cl>O.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:3]1[C:17]([O:45][CH:41]1[CH2:52][C:38](=[O:37])[C:39]([CH2:44][CH:43]=[CH2:42])=[C:40]1[CH3:55])=[O:18]

Participants

7

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 13188366(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[(Z) 3-(2,2,2trifluoroethoxy)-3-oxo-1-propenyl]-cyclopropane-carboxylateHCID 88650986(1R,cis)2,2-dimethyl-3[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylic acid chloride

Product 1

HCID 867435302-methyl-4-oxo-3-(2propenyl)-2-cyclopenten-1-yl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

1 g of (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylic acid chloride was added to a mixture of 450 mg of (S) 3-(2-propenyl)-1-hydroxy-2-methyl-4-oxo-cyclopent-2-en-1-yl, 20 ml of benzene and 0.6 ml of pyridine and the mixture was stirred for 6 hours and was then poured into a mixture of iced water and N hydrochloric acid. The mixture was extracted with benzene and the combined benzene phases was washed with water, dried and evaporated to dryness. The 1.5 g of residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain (1S) 2-methyl-4-oxo-3-(2propenyl)-2-cyclopenten-1-yl (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylate having a specific rotation of [α]D20 =+37°±2.5 (c=0.5% in benzene).

Workup

  1. extractionThe mixture was extracted with benzene
  2. washthe combined benzene phases was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe 1.5 g of residue was chromatographed over silica gel
  6. washwas eluted with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-126a642de6bb4f08a94c9cbba93fe477
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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