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

HRID 252046노트

반응식

HRID 252046 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

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%)

후처리

  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)

출처 및 근거

ORD 기록
ord-c847e169d6cd4642871842fcc15b9c0a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868002B2

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