Sodium sulfate decahydrate → 4-({[5'-(hydroxymethyl)-2,2',6-trimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol

HRID 508014Notes

Reaction equation

HRID 508014 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[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([C:24](OC)=[O:25])[CH:18]=3)=[C:12]([CH3:28])[CH:11]=2)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:25][CH2:24][C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:17]([C:13]2[C:12]([CH3:28])=[CH:11][C:10]([O:9][CH2:8][C:2]3([OH:1])[CH2:3][CH2:4][S:5][CH2:6][CH2:7]3)=[CH:15][C:14]=2[CH3:16])[CH:18]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23157321methyl 4'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6,6'-trimethylbiphenyl-3-carboxylate

Product 1

HCID 231574284-({[5'-(hydroxymethyl)-2,2',6-trimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-olYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4′-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6,6′-trimethylbiphenyl-3-carboxylate (191 mg, 0.48 mmol) in anhydrous tetrahydrofuran (3 mL) was added lithium aluminum hydride (34.2 mg, 0.72 mmol) under ice-cooling, and the mixture was stirred overnight at room temperature. Anhydrous tetrahydrofuran (10 mL) was added to the reaction solution, and the solution was ice-cooled. Sodium sulfate decahydrate (232 mg, 0.72 mmol) was added, and the mixture was stirred at room temperature for 2 hr. The precipitated insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure to give the title compound (182 mg, yield 100%) as a colorless amorphous powder.

Workup

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

Sources & evidence

ORD record
ord-d4104b60dd4649e7852f4b8b9a0c7a74
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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