Water → 1-(((S)-2-(Bromomethyl)-3-methylbutoxy)methyl)benzene

HRID 1522951ノート

反応式

HRID 1522951 の反応式
[CH2:1]([O:8][CH2:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)([Br:18])=O.O>CN(C)C=O>[CH2:1]([O:8][CH2:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11][Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 24613Phosphorus oxybromideHCID 68782329(R)-2-(benzyloxymethyl)-3-methylbutan-1-ol

生成物 1

HCID 117159911-(((S)-2-(Bromomethyl)-3-methylbutoxy)methyl)benzene収率 81.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Dissolve (R)-2-(benzyloxy-methyl)-3-methyl butanol (15.6 g, 75 mmol) in N,N-dimethyl formamide (246 ml), add phosphorus oxybromide (22.58 g, 78.75 mmol) in droplets slowly and control the temperature below 50° C. in that process, and then let them to react at 50° C. for 3 hours. Cool down to room temperature, and pour the reactant liquid into water (246 ml) slowly, extract with normal hexane for three cycles, combine the normal hexane layers, wash twice with saturated sodium bicarbonate and saturated sodium chloride respectively, dry the organic layer with anhydrous sodium sulfate, filter, and condense the filtrate so as to obtain 18.1 g of oily matter. Treat the oil matter by reduced pressure distillation to obtain 16.6 g of colorless transparent liquid; the yield is 81.1%, and the chiral purity is ≧99.9%.

後処理

  1. customthe temperature below 50° C.
  2. customto react at 50° C. for 3 hours
  3. extractionextract with normal hexane for three cycles
  4. washwash twice with saturated sodium bicarbonate and saturated sodium chloride respectively
  5. dry with materialdry the organic layer with anhydrous sodium sulfate
  6. filtrationfilter
  7. customcondense the filtrate so as
  8. customto obtain 18.1 g of oily matter
  9. additionTreat the oil matter
  10. distillationby reduced pressure distillation

出典と根拠

ORDレコード
ord-dd6fbddcd20641879102440530630273
出典データセット
uspto-grants-2015_07
特許番号
US09079839B2

反応ノート

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