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

HRID 1642611ノート

反応式

HRID 1642611 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d0152188d15c46dfba44dab63735e4e7
出典データセット
uspto-grants-2012_02
特許番号
US08119666B2

反応ノート

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