Pyridine → HCID 54376102, compound

HRID 435953Notes

Reaction equation

HRID 435953 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-1-octenyl)cyclopentyl]heptanoate, described in Example 92, in methylene chloride (50 ml). The mixture is stirred for 1 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 1 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-77126a69ad8a46da800c5aa89b803bc7
Source dataset
uspto-grants-1977_02
Patent number
US04007171

Reaction notes

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