2,2-Dimethyl-7-phenyl-7-pyridin-3-yl-hept-6-enoic acid → (E)-2,2-dimethyl-7-phenyl-7-(3-pyridyl)-6-heptenoic acid

HRID 463058Notes

Reaction equation

[CH3:1][C:2]([CH3:23])([CH2:6][CH2:7][CH2:8]/[CH:9]=[C:10](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:3]([OH:5])=[O:4]>Cl>[CH3:1][C:2]([CH3:23])([CH2:6][CH2:7][CH2:8]/[CH:9]=[C:10](\[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)/[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[C:3]([OH:5])=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

(Z)-2,2-dimethyl-7-phenyl-7-(3-pyridyl)-6-heptenoic acid (0.1 g) was dissolved in 18% aqueous hydrochloric acid (1 ml) and the solution was heated at 100° C. for 21 hours. Extraction, separation and concentration in the conventional manner gave the crude product. High performance liquid chromatography of this crude product revealed that its E isomer/Z isomer ratio was E/Z=63:28. This crude product (85 mg) was subjected to preparative high performance chromatography to give (E)-2,2-dimethyl-7-phenyl-7-(3-pyridyl)-6-heptenoic acid (46 mg).

Workup

extractionExtraction, separation and concentration in the conventional manner
customgave the crude product

Sources & evidence

ORD record: ord-9ed3b2edfe294ba081f3760a005a9241
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04518602

Reaction notes

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