Benzyl Bromide → (2R,3R)-3-(Benzyloxy)butan-2-OL

HRID 1027846

반응식

HRID 1027846 반응식
[CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+]>[CH2:7]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 2

HCID 7498Benzyl BromideHCID 225936(2R,3R)-Butanediol

생성물 1

HCID 12695195(2R,3R)-3-(Benzyloxy)butan-2-OL수율 43%

시약·촉매·용매 3

HCID 5234Sodium Chloride용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

5.00 g (44.6 mmol) of potassium tert.-butylate was added to a solution of 4.00 g (44.4 mmol) (2R,3R)-butane-2,3-diol in 300 ml THF at room temperature and the mixture was refluxed for 15 minutes. The mixture was cooled to approx. 50° C. and 5.3 ml (44.6 mmol) benzyl bromide was added. It was refluxed for 3 hours, and was then stirred overnight at room temperature. The mixture was diluted with ethyl acetate and sodium chloride solution and then washed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×). The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified chromatographically (hexane/ethyl acetate 1:1). 3.41 g (18.9 mmol; yield: 43%) of the product was obtained.

후처리

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureIt was refluxed for 3 hours
  3. washwashed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue obtained
  8. customwas purified chromatographically (hexane/ethyl acetate 1:1)
  9. custom3.41 g (18.9 mmol; yield: 43%) of the product was obtained

출처 및 근거

ORD 기록
ord-86aacf66949b4bfb82e5ce76d2573ccc
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735412B2

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