Citric Acid → [4-Hydroxy-3'-(hydroxymethyl)-6-methylbiphenyl-2-yl]methyl acetate

HRID 453440ノート

反応式

HRID 453440 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12]C(=O)C)[CH:9]=[C:8]([CH3:16])[C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=1)(=[O:3])[CH3:2].O1CCCC1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]([CH3:16])[C:7]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][OH:24])[CH:18]=1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 59342569(4-Acetoxy-3'-formyl-6-methylbiphenyl-2-yl)methyl acetate

生成物 1

HCID 59342611[4-Hydroxy-3'-(hydroxymethyl)-6-methylbiphenyl-2-yl]methyl acetate収率 71.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (4-acetoxy-3′-formyl-6-methylbiphenyl-2-yl)methyl acetate (1.63 g, 4.99 mmol) in a mixed solvent of tetrahydrofuran (10 mL) and methanol (5 mL) was added sodium borohydride (90%, 0.210 g, 5.00 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 3 hr under nitrogen atmosphere. Aqueous citric acid solution was added to the reaction mixture, and the mixture was 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=20:80-80:20) to give the title compound (1.02 g, yield 71%) as a colorless oil.

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted 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=20:80-80:20)

出典と根拠

ORDレコード
ord-d7cd7898385e4bd9ab59e77663229662
出典データセット
uspto-grants-2013_07
特許番号
US08492430B2

反応ノート

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