HCID 13390089, compound → HCID 86743531, compound

HRID 1639430Notes

Reaction equation

HRID 1639430 reaction equation
[CH3:1][C:2]1(C)[C@@H](/C=C\C(=O)OC2C=CC=CC=2)[C@H:3]1C(O)=O.[CH3:20][C:21]1([CH3:54])[C@@H:23](/[CH:24]=[CH:25]\[C:26](=[O:34])[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:22]1[C:35]([O:37][C@H:38](C#N)[C:39]1[CH:44]=C[CH:42]=[C:41]([O:45]C2C=CC=CC=2)[CH:40]=1)=[O:36].CC1(C)C(/C=C\C(=O)OC2C=CC=CC=2)C1C([O-])=O>>[CH3:20][C:21]1([CH3:54])[C@@H:23](/[CH:24]=[CH:25]\[C:26](=[O:34])[O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:22]1[C:35]([O:37][CH:38]1[CH2:42][C:41](=[O:45])[C:40]([CH2:3][CH:2]=[CH2:1])=[C:39]1[CH3:44])=[O:36]

Participants

4

Reactant 3

HCID 13390089HCID 13390089, compoundHCID 86743532HCID 86743532, compoundHCID 86743533HCID 86743533, compound

Product 1

HCID 86743531HCID 86743531, compoundYield 189.6%

Procedure

Using the procedure of Example 2, 1.5 g of (1R,cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-phenoxy-1-propenyl]-cyclopropane-carboxylic acid and 1 g of (S) 3-(2-propenyl)-1-hydroxy-2-methyl-4-oxo-cyclopent-2-en-1-yl were reacted to obtain 1.6 g of (1S) 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl (1R, cis) 2,2-dimethyl-3-[(Z) 3-oxo-3-phenoxy-1-propenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+66°±2.5 (c=0.5% in benzene).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-a2f824e5ca0240efb44c73d216226d0a
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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