Tetrahydrofuran → HCID 12595526, compound

HRID 462289Notes

Reaction equation

HRID 462289 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])([CH2:9][CH2:10][C:11]([OH:13])=O)[CH2:4][CH2:5][C:6]([OH:8])=[O:7])#[N:2].Cl[C:22]1C=CC(C(C#N)(CCC(O)=O)CCC(O)=O)=CC=1.O1CCCC1.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:6]([CH:5]1[CH2:4][C:3]([C:1]#[N:2])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH2:9][CH2:10][C:11]1=[O:13])([O:8][CH3:22])=[O:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 18789783HCID 18789783, compoundHCID 204534054-(p-Chlorophenyl)-4-cyanopimelic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 12595526HCID 12595526, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part B, but substituting 21.76 gm. (0.0715 mole) of the dimethyl ester of 4-cyano-4-(o-tolyl)pimelic acid (prepared in Part A, above) for the 34.97 gm. of the dimethyl ester of 4-(p-chlorophenyl)-4-cyanopimelic acid and using 460 ml. of the tetrahydrofuran, 16.3 gm. (0.145 mole) of the potassium tert-butoxide, and 115 ml. of the 2.5 N aqueous acetic acid instead of the 700 ml., the 24.4 gm. and the 175 ml., respectively, there is prepared 18.0 gm. (93% yield) of 2-carbomethoxy-4-cyano-4-(o-tolyl)cyclohexanone as a crystalline solid having a melting range at 107° to 113° C.

Workup

  1. custom, respectively, there is prepared 18.0 gm

Sources & evidence

ORD record
ord-4793807d9fdf4e839055cb788e4a3ebc
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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