Potassium Carbonate → methyl 4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6,6'-trimethylbiphenyl-3-carboxylate

HRID 508013Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)=[C:4]([CH3:20])[CH:3]=1.[O:21]1[C:23]2([CH2:28][CH2:27][S:26][CH2:25][CH2:24]2)[CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[OH:21][C:23]1([CH2:22][O:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([C:9]3[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]([O:18][CH3:19])=[O:17])[CH:10]=3)=[C:4]([CH3:20])[CH:3]=2)[CH2:28][CH2:27][S:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 4′-hydroxy-2′,6,6′-trimethylbiphenyl-3-carboxylate (199 mg, 0.74 mmol) and 1-oxa-6-thiaspiro[2.5]octane (116 mg, 0.89 mmol) in N,N-dimethylformamide (2.5 mL) was added potassium carbonate (123 mg, 0.89 mmol) and the mixture was stirred overnight at 100° C. Brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (191 mg, yield 64%) as a colorless oil.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-6aeb5b0ab3d14adcbbdae1c40b195004
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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