HCID 86677004, compound → HCID 86677003, compound

HRID 537389Notes

Reaction equation

HRID 537389 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13](=[CH:15][CH2:16][CH2:17][CH:18]([CH3:33])[CH2:19][CH:20]([OH:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31])[CH3:14]>ClCCl>[CH3:14][C:13](=[CH:15][CH2:16][CH2:17][CH:18]([CH3:33])[CH2:19][C:20](=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31])[CH3:12]

Participants

4

Reactant 2

HCID 86677004HCID 86677004, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86677003HCID 86677003, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (15 g, 0.07 mol) was added to a solution of 2,6-dimethyl-nonadeca-2,18-dien-8-ol (18 g, 0.058 mol, prepared as above in EXAMPLE III) in dichloromethane (100 mL) and stirred at room temperature for 6 hours. Silica gel (˜15 g) was added to the reaction mixture, and the resulting mixture was concentrated via rotary evaporation. The crude concentrated mixture was scrapped away from the flask with a spatula and filtered through a silica gel plug using ethyl acetate (100%). The filtrate was concentrated and chromatographed on silica gel with ethyl acetate in hexanes (2%) as the eluent providing 2,6-dimethyl-nonadeca-2,18-dien-8-one as a colorless oil (15 g).

Workup

  1. additionSilica gel (˜15 g) was added to the reaction mixture
  2. concentrationthe resulting mixture was concentrated via rotary evaporation
  3. concentrationThe crude concentrated mixture
  4. filtrationfiltered through a silica gel plug
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel with ethyl acetate in hexanes (2%) as the eluent

Sources & evidence

ORD record
ord-f00b4eab4a58413583f7dfc37695fbfa
Source dataset
uspto-grants-2014_10
Patent number
US08859820B1

Reaction notes

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