HCID 10071149, compound → HCID 14524037, compound

HRID 2270454Notes

Reaction equation

HRID 2270454 reaction equation
[CH3:1][O:2][C:3](=[O:28])/[CH:4]=[C:5]1\[C:6](=[CH2:27])[C@@H:7]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:8][C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:10]\1>CCCCCC>[CH3:1][O:2][C:3](=[O:28])/[CH:4]=[C:5]1/[C:6](=[CH2:27])[C@@H:7]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:21])[CH3:22])[CH2:8][C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:10]/1

Participants

3

Reactant 1

HCID 10071149HCID 10071149, compound

Product 1

HCID 14524037HCID 14524037, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 4.45 g (0.01043 mole) of Z-(3S,5R)-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-acetic acid methyl ester (X) (A. Mourino, et al., Tetrahedron Letters, 38, pgs. 4713-4716 (1997)) in 100 ml hexane was irradiated with a UV-lamp for 3 hours. Evaporation gave 4.25 g (95.5%) of the title compound as colorless oil. NMR (CDCl3): δ0.06 (s, 3H), 0.07 (s, 9H), 0.85 (s, 9H), 0.89 (s, 9H), 1.76 (m, 1H), 1.84 (m, 1H), 2.70 (m, 1H), 3.36 (m, 1H), 3.70 (s, 3H), 4.26 (m, 1H), 4.58 (m, 1H), 5.07 (m, 2H), 5.91 (brs, 1H).

Workup

  1. customEvaporation

Sources & evidence

ORD record
ord-b4b001f3ab0449049edba50c92bb25c1
Source dataset
uspto-grants-2001_12
Patent number
US06331642B1

Reaction notes

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