Hydrochloric Acid → Methyl 5-phenyl-3,5-dihydroxypentanoate

HRID 2226275

반응식

HRID 2226275 반응식
[C:1]1([CH:7]([OH:16])[CH2:8][C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].O.Cl>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].[Cl-].[Ti+4]>[C:1]1([CH:7]([OH:16])[CH2:8][CH:9]([OH:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 11020460Methyl 5-hydroxy-3-oxo-5-phenylpentanoate

생성물 1

HCID 19003817Methyl 5-phenyl-3,5-dihydroxypentanoate수율 70%

시약·촉매·용매 2

HCID 3084342Chlorotitanium triisopropoxide촉매HCID 887Methanol용매2회

반응 조건

온도
-10 °C

실험 절차

1.03 g of methyl 5-phenyl-5-hydroxy-3-oxo-pentanoate is dissolved in 40 cm3 methanol. The solution is cooled to -10° C. and then 1.3 cm3 of 95% titanium chloride triisopropoxide (4.5 mmol) are added. The mixture is stirred for 20 minutes at -10° C. and then 329.6 mg of 95% sodium cyanoborohydride (50 mmol) are added. The mixture is stirred for 3 hours at a temperature between -5° and 0° C. 10 cm3 of water and 1 cm3 of concentrated hydrochloric acid are then added. After evaporation of the methanol under reduced pressure, the mixture is taken up in 70 cm3 of dichloromethane. The organic phase is washed with 2 times 50 cm3 of water and then dried over sodium sulphate. After filtration and concentration under reduced pressure, the product obtained is treated twice with methanol. There is thus obtained, with a yield of 70%, 720 mg of methyl 5-phenyl-3,5-dihydroxypentanoate for which the syn/anti ratio is equal to 93/7.

후처리

  1. stirringThe mixture is stirred for 3 hours at a temperature between -5° and 0° C
  2. customAfter evaporation of the methanol under reduced pressure
  3. washThe organic phase is washed with 2 times 50 cm3 of water
  4. dry with materialdried over sodium sulphate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. customthe product obtained

출처 및 근거

ORD 기록
ord-12c19bba2d87451cac8e7ff307c58b4f
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05347039

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