Hydrochloric Acid → HCID 19378167, compound

HRID 2211014Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][S:8][CH2:9][CH:10]2[O:15][C:13](=[O:14])[C:12](=[CH2:16])[CH2:11]2)=[CH:5][CH:4]=1.[Cl-].[NH4+].Cl>C1COCC1.C([Li])CCC.CCCCCC>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][S:8][CH2:16][CH:12]2[CH2:11][CH:10]([CH2:9][S:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=3)[O:15][C:13]2=[O:14])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 4-methoxybenzylmercaptane (0.47 ml) in THF (6 ml), n-butyllithium/n-hexane (1.6N, 0.18 ml) and 4-(4-methoxybenzylthiomethyl)-2-methylene-4-butanolide (compound No.1-2, 0.76 g) dissolved in THF (4 ml) was added dropwise at about -78° C. under nitrogen atmosphere. The mixture was stirred for an additional 15 minutes at -78° C. After restoring to room temperature, saturated aqueous ammonium chloride solution was added to the mixture. The mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give crude oil of the titled compound as a mixture of cis and trans forms. The ratio of cis and trans products is 2.2:1.0.

Workup

additionwas added dropwise at about -78° C. under nitrogen atmosphere
customAfter restoring to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated sodium chloride solution
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-63fb17f1abdc40ee9cc314d113dc74d1
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05461158

Reaction notes

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