Tetrahydrofuran → Methyl 5-cyano-5-(3,4-dimethoxyphenyl)-2-oxocyclohexanecarboxylate

HRID 462279Notes

Reaction equation

HRID 462279 reaction equation
[C:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)([CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:4][CH2:5][C:6]([OH:8])=O)#[N:2].Cl[C:25]1C=CC(C(C#N)(CCC(O)=O)CCC(O)=O)=CC=1.O1CCCC1.CC(C)([O-])C.[K+]>C(O)(=O)C>[C:11]([CH:10]1[CH2:9][C:3]([C:1]#[N:2])([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[CH2:4][CH2:5][C:6]1=[O:8])([O:13][CH3:25])=[O:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 20453334HCID 20453334, compoundHCID 204534054-(p-Chlorophenyl)-4-cyanopimelic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 13345275Methyl 5-cyano-5-(3,4-dimethoxyphenyl)-2-oxocyclohexanecarboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part B, but substituting 34.25 gm. (0.098 mole) of the dimethyl ester of 4-cyano-4-(3,4-dimethoxyphenyl)pimelic acid (prepared in Part A, above) for the dimethyl ester of 4-(p-chlorophenyl)-4-cyanopimelic acid and using 640 ml. of the tetrahydrofuran, 22.0 gm. (0.196 mole) of the potassium tert-butoxide and 155 ml. of the 2.5 N of the aqueous acetic acid instead of the 700 ml. the 24.4 gm. (0.218 mole), and the 175 ml. respectively, there is prepared 29.2 gm. (94% yield) of 2-carbomethoxy-4-cyano-4-(3,4-dimethoxyphenyl)cyclohexanone as crystals having a melting range of 110° to 113° C. An analytical sample recrystallized from a mixture of ethyl acetate and cyclohexane melts in the range of 112.5° to 114.5° C.

Workup

  1. customrespectively, there is prepared 29.2 gm

Sources & evidence

ORD record
ord-6797d6b7dd824bbbb2d47a5684732979
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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