Sodium sulfate decahydrate → {4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methanol

HRID 1691526Notes

Reaction equation

HRID 1691526 reaction equation
[O:1]=[S:2]1(=[O:27])[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22](OC)=[O:23])[CH:17]=3)=[C:11]([CH3:26])[CH:10]=2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:1]=[S:2]1(=[O:27])[CH2:3][CH2:4][CH:5]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[CH:17]=3)=[C:11]([CH3:26])[CH:10]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 59342580methyl 4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-carboxylate

Product 1

HCID 59342608{4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methanolYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4′-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2′,6′-dimethylbiphenyl-3-carboxylate (0.128 g, 0.33 mmol) in tetrahydrofuran (2 mL) was added lithium aluminum hydride (80%, 15.7 mg, 0.33 mmol) in small portions under ice-cooling, and the mixture was stirred at the same temperature for 1.5 hr. Sodium sulfate 10 hydrate (0.106 g, 0.33 mmol) was added to the reaction mixture in small portions, and the mixture was stirred at room temperature for 1 hr. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (0.111 g, yield 93%) as a colorless amorphous powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. filtrationThe insoluble material was filtered off through celite
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9042a3991c3a4544b435626d2b5449de
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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