Sodium Hydroxide → 5,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid

HRID 1004916Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([O:19]C)=[O:18])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CCO.C1COCC1>[CH3:1][C:2]1([CH3:21])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate (Compound E5, 430.0 mg, 1.44 mmol) in 3.0 mL of EtOH and 3.0 mL THF was added NaOH (240.0 mg, 6.00 mmol; 3.0 mL of a 2N aqueous solution). The resulting solution was warmed to 35° C. for 6 h, cooled to room temperature and quenched with 1M HCl. The mixture was extracted with EtOAc and the combined organic layers washed with H2O and saturated aqueous Naa before being dried over MgSO4. Removal of the solvents under reduced pressure afforded the title compound as a pale yellow solid.

Workup

temperaturecooled to room temperature
customquenched with 1M HCl
extractionThe mixture was extracted with EtOAc
washthe combined organic layers washed with H2O and saturated aqueous Naa
dry with materialbefore being dried over MgSO4
customRemoval of the solvents under reduced pressure

Sources & evidence

ORD record: ord-d2711e92567b447aa955280dec868457
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051731

Reaction notes

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