Pyridine → HCID 54376102, compound

HRID 1288092Notes

Reaction equation

HRID 1288092 reaction equation
N1C=CC=CC=1.[Cr](O)(O)(=O)=O.[OH:12][CH:13]1[CH2:17][CH2:16][CH:15](/[CH:18]=[CH:19]/[C:20]([OH:27])([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:14]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35]>C(Cl)Cl>[OH:27][C:20]([CH3:26])([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:19]=[CH:18][C@@H:15]1[CH2:16][CH2:17][C:13](=[O:12])[C@H:14]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24425Chromic AcidHCID 20326993HCID 20326993, compound

Product 1

HCID 54376102HCID 54376102, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dry pyridine (5.85 ml) in methylene chloride (135 ml, purified by shaking with H2SO4, and dried over CaO, and distilled) is added chromic acid (4 g) at 15° C. The mixture is stirred for 20 min. To this mixture is added a solution of the compound of formula 1 in which R2 is methyl, methyl trans-7-[2-hydroxy-5-(3-hydroxy-3-methyl-l-octenyl)cyclopentyl]heptanoate, described in Example 92, in methylene chloride (50 ml). The mixture is stirred for one hour. The reaction mixture is filtered and the collected slurry on the filter pad is washed with more methylene chloride. The organic phase of the filtrate and washing are combined and washed with water, dried (Na2SO4) and the solvent concentrated, to yield the crude product. Chromatography of the product on a silica gel column affords the title compound, identical to the product of the same name described in Example 91.

Workup

  1. stirringThe mixture is stirred for one hour
  2. filtrationThe reaction mixture is filtered
  3. washthe collected slurry on the filter pad is washed with more methylene chloride
  4. washThe organic phase of the filtrate and washing
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationthe solvent concentrated
  8. customto yield the crude product

Sources & evidence

ORD record
ord-efb740c2d60548bca7f583583d4064b0
Source dataset
uspto-grants-1976_10
Patent number
US03987081

Reaction notes

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