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

HRID 273389Notes

Reaction equation

HRID 273389 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) at room temperature with stirring and the mixture was stirred at 100° C. for 12 hrs. The reaction mixture was concentrated under reduced pressure. To the residue was added 1 M hydrochloric acid to neutralize the solution and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, concentrated under reduced pressure and crystallized by adding diisopropyl ether to the obtained oil. 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. for 12 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added 1 M hydrochloric acid
  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. customcrystallized
  8. additionby adding diisopropyl ether to the obtained oil
  9. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-2780be9b2a004cf9a62fea5c16881bbe
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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