Citric Acid → (2',6'-Diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

HRID 1908903Notes

Reaction equation

HRID 1908903 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:5]([CH2:17][CH3:18])[C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[CH:20]=1)[CH3:2].CO.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH2:17]([C:5]1[CH:6]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=1)[CH3:18]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 593425632',6'-Diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde

Product 1

HCID 59342594(2',6'-Diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2′,6′-diethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (2.86 g, 7.64 mmol) in a mixed solvent of methanol (8 mL) and tetrahydrofuran (16 mL) was ice-cooled, sodium borohydride (90%, 0.161 g, 3.82 mmol) was added, and the mixture was stirred for 2 hr under nitrogen atmosphere. The reaction mixture was treated with 10% aqueous citric acid solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:80-80:20), and the obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (2.41 g, yield 84%) as colorless crystals.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:80-80:20)
  7. customthe obtained crystals were recrystallized from heptane-ethyl acetate

Sources & evidence

ORD record
ord-2e5bdfffd76f42e995b816a0ba9749d5
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

Loading…