Tetrahydrofuran → 4-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol

HRID 1908872Notes

Reaction equation

HRID 1908872 reaction equation
[OH:1][C:2]1([CH2:8][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)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.O1CCCC1.[BH4-].[Na+]>CO>[OH:24][CH2:23][C:19]1[CH:18]=[C:17]([C:13]2[C:12]([CH3:25])=[CH:11][C:10]([O:9][CH2:8][C:2]3([OH:1])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]3)=[CH:15][C:14]=2[CH3:16])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 231574564'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 231571864-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-olYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4′-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.12 g, 5.95 mmol) in a mixed solvent of tetrahydrofuran (8 mL) and methanol (4 mL) was added sodium borohydride (0.225 g, 5.95 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 20 min. The reaction solution was concentrated under reduced pressure, aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (1.87 g, yield 88%) as colorless crystals.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure, aqueous ammonium chloride solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03995a45d44e4732b8956cc75c276c78
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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