Pyridine → HCID 13055588, compound

HRID 1703200Notes

Reaction equation

HRID 1703200 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][C:9](=[O:47])[CH2:10][CH:11]([OH:46])[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]1[C@@H:20](/[CH:21]=[CH:22]/[C@@H:23]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:24]([CH3:30])([CH3:29])[CH2:25][CH2:26][CH2:27][CH3:28])[C@H:19]([O:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[CH2:18][C:17]1=[O:45].S(=O)(=O)(O)[O-].[Na+]>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[CH3:7][O:8][C:9](=[O:47])[CH2:10][C:11](=[O:46])[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]1[C@@H:20](/[CH:21]=[CH:22]/[C@@H:23]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[C:24]([CH3:29])([CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[C@H:19]([O:38][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[CH2:18][C:17]1=[O:45]

Participants

6

Reactant 3

HCID 1049PyridineHCID 516919Sodium BisulfateHCID 13055586HCID 13055586, compound

Product 1

HCID 13055588HCID 13055588, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Under an atmosphere of nitrogen, 100 mg of chromium trioxide and 0.5 g of infusorial earth were added to 0.162 ml of pyridine in 3 ml of methylene chloride, and the mixture was stirred for 15 minutes at room temperature. 55 mg of the 3-hydroxy compound (prepared as described in Example 1) in 1 ml of methylene chloride were added thereto at 0° C., and the mixture was stirred for 20 minutes at the same temperature. To the reaction solution obtained was added 1 g of sodium bisulphate and, after stirring for 20 minutes at 0° C., the mixture was filtered through a magnesium sulphate layer. The filtrate was concentrated under reduced pressure. The residue obtained was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (6:1) as eluent to obtain 42 mg of the title compound having the following physical characteristics:

Workup

  1. stirringat 0° C., and the mixture was stirred for 20 minutes at the same temperature
  2. customTo the reaction solution obtained
  3. stirringafter stirring for 20 minutes at 0° C.
  4. filtrationthe mixture was filtered through a magnesium sulphate layer
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by column chromatography on silica gel using
  8. additiona mixture of cyclohexane and ethyl acetate (6:1) as eluent

Sources & evidence

ORD record
ord-425a02627e1041e9bde79ea5a2621a06
Source dataset
uspto-grants-1982_09
Patent number
US04351846

Reaction notes

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