Ozone → 3-phenylbutane-1,3-diol

HRID 450963ノート

反応式

HRID 450963 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 113240913-phenylbutane-1,3-diol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-39e87bb1bc9548cca74618f4df874bcb
出典データセット
uspto-grants-2013_07
特許番号
US08487094B2

反応ノート

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