Tetrahydrofuran → 4-(m-Anisyl)-2-carbomethoxy-4-cyanocyclohexanone

HRID 462286Notes

Reaction equation

HRID 462286 reaction equation
[CH2:1]([C:10]([C:21]#[N:22])([CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH2:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.Cl[C:24]1C=CC(C(C#N)(CCC(O)=O)CCC(O)=O)=CC=1.O1CCCC1.CC(C)([O-])C.[K+]>C(O)(=O)C>[CH2:1]([C:10]1([C:21]#[N:22])[CH2:11][CH2:12][C:13](=[O:15])[CH:17]([C:18]([O:20][CH3:24])=[O:19])[CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 204534054-(p-Chlorophenyl)-4-cyanopimelic acidHCID 20453440HCID 20453440, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 204533794-(m-Anisyl)-2-carbomethoxy-4-cyanocyclohexanoneYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following the procedure of Example 1, Part B, but substituting 30.34 gm. (0.0951 mole) of the dimethyl ester of 4-(m-anisyl)-4-cyanopimelic acid (prepared in Part A, above) for the 34.97 gm. of the dimethyl ester of 4-(p-chlorophenyl)-4-cyanopimelic acid and using 620 ml. of the tetrahydrofuran, 21.3 gm. (0.19 mole) of the potassium tert-butoxide, and 150 ml. of the 2.5 N glacial acetic acid instead of the 700 ml., the 24.4 gm. (0.218 mole), and the 175 ml., respectively, there is prepared 29.1 gm. (99% yield) of 4-(m-anisyl)-2-carbomethoxy-4-cyanocyclohexanone as a gum.

Workup

  1. custom, respectively, there is prepared 29.1 gm

Sources & evidence

ORD record
ord-da8dd276b965410ba944526c5ff536a1
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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