Tetrahydropyranyl ether → Tetrahydropyranyl ether

HRID 1395808

反応式

HRID 1395808 の反応式
[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

参加物

6

反応物 3

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

生成物 2

HCID 263182Tetrahydropyranyl etherHCID 52808896-Keto-PGE1

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-97eeed0a44514c299a7f39068ff6ad16
出典データセット
uspto-grants-1980_05
特許番号
US04205178

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