Ozone → 3-phenylbutane-1,3-diol

HRID 450963

반응식

HRID 450963 반응식
[C:1]1([C:7]([OH:12])([CH2:9][CH:10]=C)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:13]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[C:1]1([C:7]([OH:12])([CH3:8])[CH2:9][CH2:10][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 24823OzoneHCID 1437612-Phenyl-4-penten-2-olHCID 4311764Sodium borohydride

생성물 1

HCID 113240913-phenylbutane-1,3-diol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2-phenylpent-4-en-2-ol (74 g, 0.457 mol) in dry CH2Cl2 (1 L) was treated with ozone at −78° C. until the mixture turned blue. The system was then flushed with oxygen to remove excess ozone. NaBH4 (42.8 g, 1.143 mol) was added to the mixture in portions at −20° C. The mixture was stirred overnight at rt. The mixture was quenched with water and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-phenylbutane-1,3-diol (67.8 g), which was used for the next step without purification.

후처리

  1. customThe system was then flushed with oxygen
  2. customto remove excess ozone
  3. customThe mixture was quenched with water
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-39e87bb1bc9548cca74618f4df874bcb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487094B2

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