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

HRID 660542ノート

反応式

HRID 660542 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 reaction is allowed to cool to RT and the solvent is removed under reduced pressure. The crude triethylsilyl ether is immediately dissolved in MeOH (20 mL), treated with TFA (approximately 0.15 mL) and stirred for 1 h. The solvent is removed under reduced pressure and the crude alcohol is purified by silica gel chromatography using a gradient of 0-50% EtOAc/hexane as eluent to afford the title compound as a light grey solid: (M+H)+=466.

後処理

  1. customThe vessel is sealed
  2. temperatureto cool to RT
  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 0.15 mL)
  6. stirringstirred for 1 h
  7. customThe solvent is removed under reduced pressure
  8. customthe crude alcohol is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-866dddd1c4e44ce0b4edfbce5ae49412
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

反応ノート

読み込み中…