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Methanol → (3,3-Dimethoxy-1-vinylcyclobutyl)methanol

HRID 594873
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HRID 594873 반응식
[CH3:1][O:2][C:3]1([O:13][CH3:14])[CH2:6][C:5]([CH:11]=[CH2:12])([C:7](OC)=[O:8])[CH2:4]1.CC(C[AlH]CC(C)C)C.CO>C1COCC1>[CH3:14][O:13][C:3]1([O:2][CH3:1])[CH2:4][C:5]([CH2:7][OH:8])([CH:11]=[CH2:12])[CH2:6]1
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참가 물질

5

반응물 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 86724271Methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate

생성물 1

HCID 86724270(3,3-Dimethoxy-1-vinylcyclobutyl)methanol수율 81.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C
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실험 절차

To a solution of methyl 3,3-dimethoxy-1-vinylcyclobutanecarboxylate (2.02 g, 10.09 mmol) in THF (20 mL) was added DIBAL-H (1.04M in toluene, 29 mL, 30.16 mmol) at 0° C. under argon, and the mixture was stirred for 30 minutes at 0° C. To the mixture was carefully added MeOH (29 mL) and Na2SO4.10H2O (29 g), and the mixture was stirred overnight. The mixture was filtered and evaporated under reduced pressure. And the residue was diluted with hexane/EtOAc=1:1 and filtrated through the pad of silica gel and concentrated in vacuo to give (3,3-dimethoxy-1-vinylcyclobutyl)methanol (1.42 g).

후처리

  1. stirringthe mixture was stirred overnight
  2. filtrationThe mixture was filtered
  3. customevaporated under reduced pressure
  4. additionAnd the residue was diluted with hexane/EtOAc=1:1
  5. filtrationfiltrated through the pad of silica gel
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3de55fefbf3b4cda953173b8834f245d
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242973B2

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