p-Toluenesulfonic acid monohydrate → (4aR,7R,7aR)-6-methoxy-2,2-dimethyl-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-ol

HRID 2191039노트

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HRID 2191039 반응식
[OH:1][CH2:2][C@@H:3]1[C@H:7]([OH:8])[C@@H:6]([OH:9])[CH:5]([O:10][CH3:11])[O:4]1.O.[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1>CC(C)=O.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:11][O:10][CH:5]1[O:4][C@H:3]2[C@H:7]([O:8][C:13]([CH3:18])([CH3:14])[O:1][CH2:2]2)[C@H:6]1[OH:9]

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11073752HCID 11073752, 화합물

생성물 1

HCID 13833842(4aR,7R,7aR)-6-methoxy-2,2-dimethyl-tetrahydro-4H-furo[3,2-d][1,3]dioxin-7-ol수율 5,030.4%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 180Acetone용매

실험 절차

Compound 35.2 (120.45 g, 734 mmol) was dissolved in 1.5 L acetone, treated with p-toluene sulfonic acid monohydrate (0.6 g, 3.15 mmol) and CuSO4 (225 g, 1.41 mol). The mixture was stirred for 60 h. The solid was removed by filtration and washed with (3×200 mL) acetone. The filtrate and the washings were combined and neutralized with 2.5 mL concentrated ammonium hydroxide. The solvent was removed by reduced pressure and the residue was dissolved in 750 mL CH2Cl2 and washed with 3'100 mL water. The water extracts were combined and extracted with 3×100 mL CH2Cl2. The CH2Cl2 extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 0-3% MeOH in CH2Cl2 to give compound 35.3 (32.36 g, 21.6% yield).

후처리

  1. customThe solid was removed by filtration
  2. washwashed with (3×200 mL) acetone
  3. customThe solvent was removed by reduced pressure
  4. dissolutionthe residue was dissolved in 750 mL CH2Cl2
  5. washwashed with 3'100 mL water
  6. extractionextracted with 3×100 mL CH2Cl2
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washeluting with 0-3% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-3e228bb20cb0433db4b8471beab2682b
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324179B2

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