Oxiranemethanol, 3-[(phenylmethoxy)methyl]- → 3-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

HRID 400233

반응식

HRID 400233 반응식
[CH2:1]([O:8][CH2:9][CH:10]1[O:14][CH:11]1[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([Mg]Cl)[CH:16]=[CH2:17]>O1CCCC1>[CH2:17]([C:10]([OH:14])([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][CH2:12][OH:13])[CH:16]=[CH2:15]

참가 물질

4

반응물 2

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-HCID 178418473HCID 178418473, 화합물

생성물 1

HCID 189441063-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

A solution of 4-benzyloxy-2,3-epoxy-1-butanol (6.28 g, 32.37 mmol) in anhydrous tetrahydrofuran (75 mL) was added dropwise at -40° C. over a period of 45 minutes, to a 2M solution of allyl magnesium chloride (48.5 mL, 97 mmol) and tetrahydrofuran (50 mL). The solution was stirred at -40° C. for 1 hour, warmed to 0° C. and quenched by addition of aqueous ammonium chloride solution. The tetrahydrofuran layer was separated and the aqueous layer was extracted with ethyl acetate (three times). The combined organic extract was dried (magnesium sulfate), filtered and concentrated to obtain a mixture of compounds A and B.

후처리

  1. temperaturewarmed to 0° C.
  2. customquenched by addition of aqueous ammonium chloride solution
  3. customThe tetrahydrofuran layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (three times)
  5. extractionThe combined organic extract
  6. dry with materialwas dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain

출처 및 근거

ORD 기록
ord-757e5a1c8b554ab7918a14250606dd48
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827868

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