Sodium sulfate decahydrate → HCID 23157205, compound

HRID 507936Notes

Reaction equation

HRID 507936 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH3:26])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:27](OC)=[O:28])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH: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>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH3:26])=[CH:19][CH:20]=2)=[CH:13][C:12]([CH2:27][OH:28])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23157441HCID 23157441, compound

Product 1

HCID 23157205HCID 23157205, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (40 mL) of methyl 6-(benzyloxy)-4′-(2-ethoxyethoxy)biphenyl-3-carboxylate (2.0 g, 4.92 mmol) in anhydrous tetrahydrofuran was added lithium aluminum hydride (0.19 g, 5.01 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction solution was ice-cooled, and sodium sulfate decahydrate (3.0 g, 5.74 mmol) was added. The mixture was stirred at room temperature for 1 hr. The precipitated insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2-1:1), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (1.7 g, yield 91%) as colorless needle crystals.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringThe mixture was stirred at room temperature for 1 hr
  4. filtrationThe precipitated insoluble material was filtered off through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-db51367a0a95477782dd5c67eacd2b07
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…