Hydrochloric Acid → Methyl 5-cyano-5-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-oxocyclohexanecarboxylate

HRID 849698Notes

Reaction equation

C[O-].[Na+].[C:4]([C:6]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:20]=1)([CH2:13][CH2:14][C:15]([O:17]C)=O)[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])#[N:5].Cl>C1(C)C=CC=CC=1>[C:9]([CH:8]1[CH2:7][C:6]([C:4]#[N:5])([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:20]=2)[CH2:13][CH2:14][C:15]1=[O:17])([O:11][CH3:12])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of sodium methoxide (350 mL, 1.55 mol, 25% w/w in methanol) in toluene (2.45 L) heated to 80° C. under a nitrogen atmosphere was added a solution of dimethyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)pimelate (350.0 g, 0.87 mol) in toluene (1.05 L) over 10 min. The reaction was heated to 85° C. by distilling away 250 mL of solvent and was vigorously stirred under nitrogen for 2 hours. The reaction was cooled to 50° C. and was quenched with 3N (aq) HCl (700 mL, 2.1 mol). The organic layer was isolated, was washed once with deionized water (700 mL) and once with brine (700 mL). The organic layer was concentrated via low vacuum distillation to afford crude 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-one in toluene. This was dissolved in 4.2 L of dimethyl sulfoxide and used in the next step.

Workup

temperatureThe reaction was heated to 85° C.
distillationby distilling away 250 mL of solvent
temperatureThe reaction was cooled to 50° C.
customThe organic layer was isolated
washwas washed once with deionized water (700 mL) and once with brine (700 mL)
concentrationThe organic layer was concentrated via low vacuum distillation

Sources & evidence

ORD record: ord-7009749d88944d679df93d0aedd2bfaa
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06013827

Reaction notes

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