Triethylsilane → 5-(2-Benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

HRID 1642611노트

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HRID 1642611 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N:17]1[CH2:21][C:20](=[O:22])[N:19]([CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[S:18]1(=[O:30])=[O:29])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][C:16]=1[N:17]1[S:18](=[O:30])(=[O:29])[N:19]([CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[C:20](=[O:22])[CH2:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 866250473-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde

생성물 1

HCID 667566545-(2-Benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

시약·촉매·용매 1

HCID 241Benzene용매

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온도
60 °C

실험 절차

To a solution of 3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde (1.6 g, 3.6 mmol) in benzene (20 mL), in a pressure vessel, is added triethylsilane (688 μL, 4.3 mmol) and (PPh3)2Re(O)2I (63 mg, 0.072 mmol). The vessel is sealed and the reaction is stirred at 60° C. for 18 h. The mixture is allowed to cool to ambient temperature and the solvent is removed under reduced pressure. The crude triethylsilyl ether is immediately dissolved in MeOH (20 mL), treated with TFA (approximately 150 μL) and stirred for 1 h. The solvent is removed under reduced pressure and the crude alcohol is purified via silica gel chromatography using a gradient of 0-50% EtOAc/hexanes to afford of 5-(2-benzyloxy-4-hydroxymethylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one as a light gray solid: MS (M+H)+=466.

후처리

  1. customThe vessel is sealed
  2. temperatureto cool to ambient temperature
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe crude triethylsilyl ether is immediately dissolved in MeOH (20 mL)
  5. additiontreated with TFA (approximately 150 μL)
  6. stirringstirred for 1 h
  7. customThe solvent is removed under reduced pressure
  8. customthe crude alcohol is purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-d0152188d15c46dfba44dab63735e4e7
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119666B2

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