Potassium Hydroxide → HCID 19962312, compound

HRID 53392Notes

Reaction equation

[CH3:1][C:2]1([CH3:28])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]([S:25][CH2:26][CH3:27])=[CH:4][CH2:3]1.[OH-].[K+]>C(O)C>[CH3:1][C:2]1([CH3:28])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:23][CH:24]=3)=[CH:7][C:6]=2[C:5]([S:25][CH2:26][CH3:27])=[CH:4][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 150 mg (0.38 mmol) of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-ethylthionaphth-3-yl)ethynyl]benzoate (Compound 151) in 4 ml of ethanol was added 1 ml of KOH (2N aqueous solution). The solution was heated to 50° C. for two hours, cooled to room temperature, concentrated in vacuo, diluted with dichloromethane (5 ml) and acidified with 10% aqueous HCl at 0° C. The layers were separated and the aqueous layer was extracted with dichloromethane (2×). The organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Recrystallization from acetonitrile gave the title compound as a white solid.

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
additiondiluted with dichloromethane (5 ml)
customacidified with 10% aqueous HCl at 0° C
customThe layers were separated
extractionthe aqueous layer was extracted with dichloromethane (2×)
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customRecrystallization from acetonitrile

Sources & evidence

ORD record: ord-77ebe0fb6af142a2bfad59ea00c030a1
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618931

Reaction notes

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