Sodium Thiosulfate → 4-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanone

HRID 2249898ノート

反応式

HRID 2249898 の反応式
[CH3:1][C:2]1([CH:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)[O:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH2:4][O:3]1.C[N+]1([O-])CCOCC1.[O-]S([O-])(=S)=O.[Na+].[Na+]>CC#N.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:1][C:2]1([CH:10]2[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]2)[O:3][CH2:4][C:5]([CH3:8])([CH3:9])[CH2:6][O:7]1

参加物

6

反応物 3

HCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 231479574-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanol

生成物 1

HCID 231479474-(2,5,5-Trimethyl-[1,3]dioxan-2-yl)-cyclohexanone収率 85%

試薬・触媒・溶媒 2

HCID 178419074HCID 178419074、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

TPAP (161 mg, 0.05 eq.) was added to a solution of 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanol (2.22 g, 1 eq.) and NMO (2.28 g, 2 eq.) in MeCN (65 mL). The reaction mixture was stirred at room temperature overnight. Saturated aqueous solution of Na2S2O3 was added to the mixture and the resulting mixture was stirred vigorously for 15 minutes. The separated aqueous phase was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4, filtered through Celite and concentrated. The crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes) to give 4-(2,5,5-trimethyl-[1,3]dioxan-2-yl)-cyclohexanone (1.87 g, 85%).

後処理

  1. stirringthe resulting mixture was stirred vigorously for 15 minutes
  2. extractionThe separated aqueous phase was extracted with CH2Cl2
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered through Celite
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (25% to 50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-f1ee43785d28423b9951bec719b86e74
出典データセット
uspto-grants-2008_01
特許番号
US07314936B2

反応ノート

読み込み中…