Isopropanol → HCID 86738048, compound

HRID 848491Notes

Reaction equation

HRID 848491 reaction equation
[OH:1][CH:2]([CH3:39])[CH2:3][CH:4]([CH:11]1[CH:15]([OH:16])[CH2:14][CH:13]([CH:17]=[CH:18][CH:19]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:12]1[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH:5]1[O:10][CH2:9][CH2:8][CH2:7][O:6]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[O:1]=[C:2]([CH3:39])[CH2:3][CH:4]([CH:11]1[C:15](=[O:16])[CH2:14][CH:13]([CH:17]=[CH:18][CH:19]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:12]1[O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH:5]1[O:10][CH2:9][CH2:8][CH2:7][O:6]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 86738049HCID 86738049, compoundHCID 131709961Jones' reagent

Product 1

HCID 86738048HCID 86738048, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.45 g of 1[4(3-hydroxy-1(1,3-dioxa-2-cyclohexyl)butyl]-2(3-tetrahydropyranyloxy-1-octenyl)-3(tetrahydropyranyloxy)-5-hydroxy-cyclopentane (IV) (Example 3) were dissolved in 30 ml of acetone. At -20° to -25° C., 2 ml of Jones reagent (2.1 g of chromic acid, 6 ml of water, 1.7 ml of concentrated sulfuric acid) were added under argon. The mixture was stirred for 30 minutes, 3 ml of isopropanol were added and stirring was continued for a further 10 minutes to destroy the oxidation reagent in excess. Next, 100 ml of methylene chloride and 100 ml of water were added, the mixture was shaken and the phases were separated. The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure at a temperature of at most +5° C. 0.32 g of compound VIII in the form of an almost colorless clear oil was obtained.

Workup

  1. stirringstirring
  2. waitwas continued for a further 10 minutes
  3. customto destroy the oxidation reagent in excess
  4. additionNext, 100 ml of methylene chloride and 100 ml of water were added
  5. stirringthe mixture was shaken
  6. customthe phases were separated
  7. dry with materialThe organic phase was dried with MgSO4
  8. customthe solvent was removed under reduced pressure at a temperature of at most +5° C

Sources & evidence

ORD record
ord-9d251e2dbc6d4a12a987818b67eb375a
Source dataset
uspto-grants-1981_10
Patent number
US04296121

Reaction notes

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