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1,8-Diazabicyclo(5.4.0)undec-7-ene → (Z)-2,2-Dimethyl-5-(tert-butyldimethylsilyloxycarbonyl-methylene)-1,3-dioxolane

HRID 2181086
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HRID 2181086 반응식
Br[C:2]1([CH2:10][C:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[O:12])[C:6](=O)[O:5][C:4]([CH3:9])([CH3:8])[O:3]1.N12CCCN=C1CCCCC2>C(Cl)(Cl)(Cl)Cl.O1CCCC1>[CH3:8][C:4]1([CH3:9])[O:5][CH2:6]/[C:2](=[CH:10]/[C:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])=[O:12])/[O:3]1
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참가 물질

5

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 235191444-Bromo-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid, tert-butyldimethylsilyl ester

생성물 1

HCID 69656326(Z)-2,2-Dimethyl-5-(tert-butyldimethylsilyloxycarbonyl-methylene)-1,3-dioxolane

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8028Tetrahydrofuran용매

실험 절차

The solution of crude 4-bromo-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid, tert-butyldimethylsilyl ester (72.4 mmol) in carbon tetrachloride (˜220 ml) was cooled to 0-5° C. and treated dropwise over 10 minutes and under good stirring with a solution of 1,8-diazabicyclo (5,4,0) undec-7-ene (12.1 g, 79.6 mmol) in dry tetrahydrofuran (125 ml). A heavy precipitate was formed which gradually became a granular solid. After 1 h, the solid obtained was filtered and washed with a small amount of tetrahydrofuran. The filtrate was concentrated under reduced pressure to give a light orange oil which was used as such for the next step.

후처리

  1. additiontreated dropwise over 10 minutes
  2. customA heavy precipitate was formed which
  3. customthe solid obtained
  4. filtrationwas filtered
  5. washwashed with a small amount of tetrahydrofuran
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a light orange oil which

출처 및 근거

ORD 기록
ord-eba46ea695e84d93806b7fb123e49392
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06890942B2

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