Potassium Hydroxide → HCID 178448011, compound

HRID 2166006Notes

Reaction equation

HRID 2166006 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C([C@H]1CC[C@H]([C@H]2CC[C@H](C(=O)C)CC2)CC1)CC.[Li+].CC([N-]C(C)C)C.CCOCC.CC(C([Si](C)(C)C)=C)=O.[OH-].[K+]>C(O)C.[Pd].C([O-])([O-])=O.[Ca+2].CCOCC.C(Cl)Cl>[CH2:1]([C@H:4]1[CH2:5][CH2:6][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH:16]3[CH2:21][CH2:20][CH2:19][C:18](=[O:22])[CH2:17]3)[CH2:12][CH2:11]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

10

Reactant 5

HCID 14797Potassium HydroxideHCID 109971413-Buten-2-one, 3-(trimethylsilyl)-HCID 86744107HCID 86744107, compoundHCID 178448028HCID 178448028, compoundHCID 178448061HCID 178448061, compound

Product 1

HCID 178448011HCID 178448011, compound

Reagents, catalysts & solvents 4

HCID 12000666Calcium Palladium CarbonateCatalystHCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6.5 g of 3-[trans-4-(trans-4-n-propyl-cyclohexyl)-cyclohexyl]-cyclohex-2-enone [m.p. 96.5°; obtainable by reacting trans-4-(trans-4-n-propycyclohexyl)-acetylcyclohexane with LDA/ether at -85°, adding 1-(trimethylsilyl)-vinyl methyl ketone at -95°, allowing the mixture to warm up to room temperature, adding methanolic KOH and working up in the customary manner (silica gel; 5:3.5:1.5 petroleum ether:methylene chloride:ether)] in 210 ml of ethanol is added to a suspension of 1.7 g of 5% Pd/CaCO3 in 75 ml of ethanol, and the mixture is stirred under hydrogen for 2 hours. Removing the catalyst and working up in the customary manner gives 3-[trans-4-(trans-4-n-propylcyclohexyl)-cyclohexyl]-cyclohexanone, m.p. 1.5°, c.p. 158.2°

Workup

  1. customat -85°
  2. customRemoving the catalyst

Sources & evidence

ORD record
ord-42553f418e204eda8254a55455ee383e
Source dataset
uspto-grants-1990_07
Patent number
US04943384

Reaction notes

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