Pyridine → HCID 54396903, compound

HRID 1578820Notes

Reaction equation

HRID 1578820 reaction equation
[CH3:1][CH:2]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:31])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:30])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].N1C=CC=CC=1.[Cr](O)(O)(=O)=O.N1C=CC=CC=1.C(Cl)Cl>[O-2].[O-2].[O-2].[Cr+6].O>[CH3:1][CH:2]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:31])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:30])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 6344DichloromethaneHCID 22134182HCID 22134182, compoundHCID 54298051HCID 54298051, compound

Product 1

HCID 54396903HCID 54396903, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To a mixture of ethyl 3,7,11,15,19-pentamethyl-6,10,14,18-eicosatetraen-2-ol-1-carboxylate (217 g) and pyridine (215 ml), chromic acid-pyridine (prepared by adding portionwise chromium trioxide (300 g) to a mixture of pyridine (480 ml) and methylene chloride (3000 ml) while cooling with ice) is added thereto, and the resultant mixture is stirred for 4 hours. The reaction mixture is added to water, and the methylene chloride layer is separated, washed with water, dried and evaporated. The residual material (203 g) is chromatographed on silica gel (1kg) using benzene to give ethyl 3,7,11,15,19-pentamethyl-6,10,14,18-eicosatetraen-2-one-1-carboxylate (172 g). IR: 1740, 1225 cm-1 (COO); 1710 cm-1 (C=O).

Workup

  1. customprepared
  2. temperaturewhile cooling with ice)
  3. additionis added
  4. customthe methylene chloride layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customThe residual material (203 g) is chromatographed on silica gel (1kg)

Sources & evidence

ORD record
ord-2e82c46484a34374b282062ff9a17359
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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