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Triethylsilane → HCID 24864236, 화합물

HRID 407872
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HRID 407872 반응식
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][C:8](=[O:12])SCC)[C:4](=[O:13])[O:3]1.C([SiH](CC)CC)C>C(Cl)Cl.[Pd]>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][CH:8]=[O:12])[C:4](=[O:13])[O:3]1
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참가 물질

5

반응물 2

HCID 12052TriethylsilaneHCID 53627664(R)-S-Ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate

생성물 1

HCID 24864236HCID 24864236, 화합물수율 98.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6344Dichloromethane용매2회

실험 절차

(R)—S-Ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (22.5 g, 103 mmol) was dissolved in CH2Cl2 (500 mL), purged with nitrogen and 10% palladium on carbon (2.19 g, 2.06 mmol) was added and triethylsilane (24.7 mL, 155 mmol) was dissolved in CH2Cl2 (20 mL) and added dropwise through an addition funnel over 30 minutes and stirred at ambient temperature overnight under nitrogen. The reaction was filtered through celite, concentrated and purified over silica gel (10 to 40% EtOAc in hexanes) to afford (R)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetaldehyde (16 g, 101 mmol, 98.1% yield) as a clear colorless oil.

후처리

  1. additionwas added
  2. additionadded dropwise through an addition funnel over 30 minutes
  3. filtrationThe reaction was filtered through celite,
  4. concentrationconcentrated
  5. custompurified over silica gel (10 to 40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-5579effdb07540a5849ba76d8695aa48
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754226B2

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