(4S,5S)-4-[(Benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane → (2R)-1-(benzyloxy)but-3-en-2-ol

HRID 1695020노트

반응식

HRID 1695020 반응식
[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:14]([CH2:15]I)OC(C)(C)[O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Zn]>[CH2:1]([O:8][CH2:9][C@H:10]([OH:11])[CH:14]=[CH2:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 1

HCID 66645664(4S,5S)-4-[(Benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane2회

생성물 1

HCID 9989803(2R)-1-(benzyloxy)but-3-en-2-ol수율 100.3%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 49.20 g of the crude (4S,5S)-4-[(benzyloxy)methyl]-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane obtained in Reference Example (1c) (136 mmol) and 26.66 g of zinc powder (408 mmol) in ethanol (420 ml) was stirred at 80° C. for three hours. After cooling the reaction mixture, the unreacted zinc powder was separated by filtration using Celite 545 and washed with ethanol. The filtrate was concentrated under reduced pressure and diluted with 1 M hydrochloric acid, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a 1.5 M sodium sulfite aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 24.29 g of the crude title compound.

후처리

  1. temperatureAfter cooling the reaction mixture
  2. customthe unreacted zinc powder was separated by filtration
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiondiluted with 1 M hydrochloric acid
  6. extractionfollowed by extraction with ethyl acetate
  7. washThen, the organic layer was washed with water
  8. dry with materiala 1.5 M sodium sulfite aqueous solution and brine and dried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-f89adf3a876a4cd6b89d681d261aea14
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158790B2

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