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

HRID 15658ノート

反応式

HRID 15658 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d050353a6c764cca9bb194ac6d2938b6
出典データセット
uspto-grants-2010_06
特許番号
US07732626B2

反応ノート

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