Diethyl Ether → HCID 178448014, compound

HRID 2166007Notes

Reaction equation

HRID 2166007 reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.[CH2:7]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH:22]3[CH2:27][CH2:26][CH2:25][C:24](=[O:28])[CH2:23]3)[CH2:18][CH2:17]2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].C(Cl)Cl.CCOCC>C1COCC1>[CH2:7]([C@H:10]1[CH2:11][CH2:12][C@H:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH:22]3[CH2:27][CH2:26][CH:25]([C:1]([O:4][CH3:5])=[O:6])[C:24](=[O:28])[CH2:23]3)[CH2:18][CH2:17]2)[CH2:14][CH2:15]1)[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 12021Dimethyl CarbonateHCID 178448011HCID 178448011, compound

Product 1

HCID 178448014HCID 178448014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.5 mmol of KH and 40 ml of dimethyl carbonate are added to a solution of 2.0 g of 3-[trans-4-(trans-4-n-propylcyclohexyl)-cyclohexyl]-cyclohexanone (Example 1) in 40 ml of THF, and the mixture is boiled for 2 hours. Customary working up (silica gel; 6.5:3:0.5 petroleum ether: methylene chloride:ether) gives methyl 4-[trans-4-(trans-4-n-propylcyclohexyl)-cyclohexyl]-2-oxocyclohexanecarboxylate, which is predominantly in the enol form, m.p. 154°, c.p. 192°.

Sources & evidence

ORD record
ord-2fdf04732bda4f0087dd54409327bb56
Source dataset
uspto-grants-1990_07
Patent number
US04943384

Reaction notes

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