Potassium Carbonate → 4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 1908871Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-oxa-6-thiaspiro[2.5]octane (6.33 g, 48.6 mmol) and 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (10.0 g, 44.2 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (6.11 g, 44.2 mmol) at room temperature, and the mixture was stirred at 100° C. for 12 hr. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give the title compound (12.3 g, yield 78%) as colorless crystals.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record: ord-cf74f332ce874899a061520363e88f9f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598226B2

Reaction notes

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