1,5-Diazabicyclo(4.3.0)non-5-ene → HCID 54266634, compound

HRID 2352430Notes

Reaction equation

HRID 2352430 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:34])[CH2:8][CH2:9][CH:10](Br)[C:11]([CH3:32])=[CH:12][CH:13]([C:23]1[C:28]([CH3:30])([CH3:29])[CH2:27][CH2:26][CH2:25][C:24]=1[CH3:31])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])(=[O:3])[CH3:2].N12CCCC1=NCCC2>C(Cl)Cl>[C:1]([O:4][CH2:5][CH:6]=[C:7]([CH3:34])[CH2:8][CH2:9][CH:10]=[C:11]([CH3:32])[CH:12]=[C:13]([C:23]1[C:28]([CH3:30])([CH3:29])[CH2:27][CH2:26][CH2:25][C:24]=1[CH3:31])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 53780798HCID 53780798, compound

Product 1

HCID 54266634HCID 54266634, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 ml flask was charged with 1.38 g (2.5 mmoles) of 1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,7-nonadiene (17) obtained in Example 14, 15 ml of methylene chloride, and 0.6 ml (5 mmoles) of 1,5-diazabicyclo[4.3.0]non-5-ene. The mixture was stirred for 5 hours under reflux. The reaction mixture was worked up by the same operation as in Example 22, to give 0.99 g (yield 84%) of 1-acetoxy-3,7-dimethyl- 9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene (19).

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-f087be9ee08844689f9f94ae5597e97f
Source dataset
uspto-grants-1989_10
Patent number
US04876400

Reaction notes

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