Tetrahydropyranyl ether → Tetrahydropyranyl ether

HRID 1395808

반응식

HRID 1395808 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])[C@@H:12]([OH:24])[CH2:11][C@H:10]1[OH:25].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:26])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14][C:15]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:16])[C:12](=[O:24])[CH2:11][C@H:10]1[OH:25].[O:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1

참가 물질

6

반응물 3

HCID 263182Tetrahydropyranyl etherHCID 52808886-Ketoprostaglandin F1 alphaHCID 131709961Jones' reagent

생성물 2

HCID 263182Tetrahydropyranyl etherHCID 52808896-Keto-PGE1

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

The reaction product from part A, containing 6-keto-PGF1α, bis(tetrahyropyranyl)ether, methyl ester corresponding to formula IV, is oxidized to compound V. A composite from several lots, weighing 0.93 g., in 20 ml. of acetone is treated at -10° C. with 2.0 ml. of Jones reagent. After stirring for 1.5 hr. the reaction mixture is quenched with isopropanol and extracted with diethyl ether. The extract is washed with brine, dried, and concentrated. The residue is subjected to silica gel chromatography, eluting with ethyl acetate (20-50%)-Skellysolve B to yield the formula-V 6-keto-PGE1, bis(tetrahydropyranyl)ether, methyl ester, 0.52 g., having Rf 0.52 (TLC on silica gel in ethyl acetate-Skellysolve B (1:1)); and infrared peaks at 1745 and 1725 cm-1 (free of OH at 3000-3500).

후처리

  1. customthe reaction mixture is quenched with isopropanol
  2. extractionextracted with diethyl ether
  3. washThe extract is washed with brine
  4. customdried
  5. concentrationconcentrated
  6. washeluting with ethyl acetate (20-50%)-Skellysolve B

출처 및 근거

ORD 기록
ord-97eeed0a44514c299a7f39068ff6ad16
출처 데이터셋
uspto-grants-1980_05
특허 번호
US04205178

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