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

HRID 453440노트

반응식

HRID 453440 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d7cd7898385e4bd9ab59e77663229662
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492430B2

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