(6S,11S)-9-hydroxy-2,6,11,15-tetramethylhexadeca-2,14-dien-8-one → (6S,11S)-2,6,11,15-tetramethylhexadeca-2,14-diene-8,9-dione

HRID 713603Notes

Reaction equation

HRID 713603 reaction equation
[OH:1][CH:2]([CH2:14][C@@H:15]([CH3:22])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:3](=[O:13])[CH2:4][C@@H:5]([CH3:12])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:20][C:19](=[CH:18][CH2:17][CH2:16][C@H:15]([CH3:22])[CH2:14][C:2](=[O:1])[C:3](=[O:13])[CH2:4][C@@H:5]([CH3:12])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH3:21]

Participants

4

Reactant 2

HCID 58098929(6S,11S)-9-hydroxy-2,6,11,15-tetramethylhexadeca-2,14-dien-8-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 58098940(6S,11S)-2,6,11,15-tetramethylhexadeca-2,14-diene-8,9-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 (7.0 g, 22.7 mmol) in 100 mL of methylene chloride was added 7.5 g of PCC. The mixture was heated to reflux. After 16 hours, the mixture was cooled to room temperature and filtered. The solution was concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel (hexane:ethyl acetate=20:1, v/v) to afford the product as a colorless oil. Yield: 3.5 g (50%). 1H NMR (400 MHz, CDCl3) δ 5.06 (m, 2H), 2.66-2.74 (dd, 2H, J=5.64, 16.71 Hz), 2.51-2.60 (dd, 2H, J=7.98, 16.73 Hz), 1.92-2.02 (m, 6H), 1.5-1.67 (s, 6H), 1.58 (s, 6H), 1.19-1.35 (m, 4H), 0.89 (d, 6H, J=6.66 Hz). 13C NMR (400 MHz, CDCl3) δ 200.05, 131.60, 124.07, 52.96, 36.94, 28.49, 25.66, 25.36, 19.71, 17.60.

Workup

  1. temperatureThe mixture was heated to reflux
  2. filtrationfiltered
  3. concentrationThe solution was concentrated under reduced pressure
  4. customThe crude compound was purified by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-6c4fe9b6f9d74d008002973eeb4fb1da
Source dataset
uspto-grants-2015_11
Patent number
US09184390B2

Reaction notes

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