Water → HCID 86740120, compound

HRID 463051Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[C:18]1(/[C:24](/[C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:25]/[CH2:26][CH2:27][CH2:28][CH2:29]I)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[C:18]1(/[C:24](/[C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:25]/[CH2:26][CH2:27][CH2:28][CH2:29][CH:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])[C:12]([O:14][CH3:15])=[O:13])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl p-methylphenylsulfonylacetate (0.43 g, 2 mmole) was dissolved in dimethylformamide, and after the solution was cooled to 0° C. under argon, sodium hydride (0.1 g) was added, followed by stirring for 10 minutes. A solution of (Z)-6-phenyl-6-(3-pyridyl)-1-iodo-5-hexene (0.8 g) in dimethylformamide (4 ml) was added to the reaction solution, and the reaction was carried out at room temperature for 3 hours. After the completion of the reaction, water (30 ml) was added, and the product was extracted with ethyl acetate. Working up in the usual procedure, the resulting product was chromatographed on silica gel, and development was effected with isopropyl ether:ethyl acetate (1:1) to yield methyl (Z)-8-phenyl-8-(3-pyridyl)-2-(p-methylphenylsulfonyl)-7-octenoate (1-c) (0.6 g, 61%).

Workup

waitthe reaction was carried out at room temperature for 3 hours
additionwas added
extractionthe product was extracted with ethyl acetate
customthe resulting product was chromatographed on silica gel, and development

Sources & evidence

ORD record: ord-9d0790e430444423b8e2b7f50df3cf24
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04518602

Reaction notes

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