Sodium Bicarbonate → 3-Benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-benzaldehyde

HRID 660541ノート

反応式

HRID 660541 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]=C)[CH:12]=[CH:11][C:10]=1[N:17]1[S:21](=[O:23])(=[O:22])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:19](=[O:30])[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:34]CC1.CC(O)(C)C.O.C([O-])(O)=O.[Na+]>CC(O)(C)C.O.O=[Os](=O)(=O)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[N:17]1[CH2:18][C:19](=[O:30])[N:20]([CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[S:21]1(=[O:23])=[O:22])[CH:15]=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 22124471t-Butanol tetrahydrofuran waterHCID 667565425-(2-Benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

To a solution of 5-(2-benzyloxy-4-vinylphenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (1.9 g, 4.3 mmol) in 1:1:1 THF/t-BuOH/H2O (60 mL) is added 1-methylmorpholine-N-oxide (551 mg, 4.74 mmol) and OsO4 (2 mL of a 2.5 wt % solution in t-BuOH, 0.17 mmol). The reaction is stirred for 4 h at RT, then diluted with water (15 mL) and treated with NalO4 (4.5 g, 21.5 mmol) and NaHCO3 (3.6 g, 43 mmol). The mixture is stirred vigorously for 1 h, then filtered through Celite. The solution is extracted with EtOAc. The organic phase is washed with sat. NaCl. The solution is dried over MgSO4 and the solvent removed under reduced pressure. The residue is purified by column chromatography using a gradient of 0-40% EtOAc/hexane to afford the title compound as a white solid: (M+NH4)+=464.

後処理

  1. stirringThe mixture is stirred vigorously for 1 h
  2. filtrationfiltered through Celite
  3. extractionThe solution is extracted with EtOAc
  4. washThe organic phase is washed with sat. NaCl
  5. dry with materialThe solution is dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe residue is purified by column chromatography

出典と根拠

ORDレコード
ord-a1e326321b06455388c58c310130653b
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

反応ノート

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