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

HRID 507975Notes

Reaction equation

HRID 507975 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 187531011-Oxa-6-thiaspiro(2.5)octaneHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 231574564'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-carbaldehydeYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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) under stirring at room temperature, and the mixture was stirred at 100° C. stirred for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was neutralized with 1 M hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Diisopropyl ether was added to the obtained oil to allow crystallization and the crystals were collected by filtration to give the title compound (12.3 g yield 78%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 100° C.
  2. stirringstirred for 12 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionDiisopropyl ether was added to the obtained oil
  8. customcrystallization
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-99470919cd714302afe7ace32ca700c1
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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