Isolongifolanone- parent → HCID 86623586, compound

HRID 1986511Notes

Reaction equation

HRID 1986511 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH3:7][C:8]1([CH3:22])[CH2:13][CH2:12][C:11](=O)[CH:10]2[C:15]([CH3:21])([CH3:20])[CH:16]3[CH2:19][C:9]12[CH2:18][CH2:17]3>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1CCCCC1>[CH:1](=[C:11]1[CH:10]2[C:15]([CH3:20])([CH3:21])[CH:16]3[CH2:19][C:9]2([CH2:18][CH2:17]3)[C:8]([CH3:22])([CH3:7])[CH2:13][CH2:12]1)[CH3:2]

Participants

5

Reactant 2

HCID 90978Isolongifolanone- parentHCID 23665647Potassium tert-butoxide

Product 1

HCID 86623586HCID 86623586, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8078CyclohexaneSolvent

Procedure

Potassium tert-butoxide (13.0 g, 0.116 mol) and ethyltriphenylphosphonium bromide (41.6 g, 0.112 mol) were added to a solution of 2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undecan-5-one (1, 20.0 g, 0.091 mol) in cyclohexane (200 ml), the reaction mixture was stirred at room temperature for 78 h and filtered through Celite®. The filtrate was concentrated and distilled under reduced pressure to give (at 95° C./0.1 mbar) 5-ethylidene-2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undecane (2b, 13.1 g, 62% yield, colourless liquid).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationThe filtrate was concentrated
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-ec800f96d66042219eeec19cad699b16
Source dataset
uspto-grants-2009_06
Patent number
US07550417B2

Reaction notes

Loading…