Water → Prostaglandin D2

HRID 258642

반응식

HRID 258642 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C.O>CC(C)=O.C(OCC)C>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@H:9]1[C:10](=[O:24])[CH2:11][C@H:12]([OH:23])[C@@H:13]1[CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21]

참가 물질

7

반응물 4

HCID 962WaterHCID 3776IsopropanolHCID 5280363DinoprostHCID 131709961Jones' reagent

생성물 1

HCID 448457Prostaglandin D2

시약·촉매·용매 2

HCID 180Acetone용매HCID 3283Diethyl Ether용매

실험 절차

PGF2α, 15-(tetrahydropyranyl ether) (2 g.) in acetone (75 ml.) is cooled to -45° C. and thereafter treated with 1.2 ml. of the Jones reagent. The mixture is stirred for 30 min. at -35° to -45° C. and thereafter treated with 0.5 ml. of isopropanol and stirred an additional 15 min. The reaction mixture is then poured into a mixture of ice, water, and diethyl ether. The mixture is then extracted with diethyl ether and the combined ethereal extracts washed with brine, and dried over sodium sulfate. After filtration removal of solvent proceeds by rotary evaporation. Crude product (1.8 g.) thereby obtained is chromatographed on 360 g. of acid washed silica gel eluting with 45 percent ethyl acetate in hexane. PGD2, 15-(tetrahydropyranyl ether) (800 mg.) is thereby obtained.

후처리

  1. additiontreated with 1.2 ml
  2. additiontreated with 0.5 ml
  3. extractionThe mixture is then extracted with diethyl ether
  4. washthe combined ethereal extracts washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration removal of solvent proceeds
  7. customby rotary evaporation
  8. customCrude product (1.8 g.) thereby obtained
  9. customis chromatographed on 360 g
  10. washof acid washed silica gel eluting with 45 percent ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ea96a0d396a2477a9d1ba6f264575d4a
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04033989

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