Water → 6,10-Dimethylundecan-2-one

HRID 637574Notes

Reaction equation

HRID 637574 reaction equation
C([CH:4]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[C:5]([CH3:9])(O)[C:6]#[CH:7])(C)=C.O1C[CH2:18][CH2:17][CH2:16]1.[OH2:20]>[Pd].FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:9][CH:5]([CH2:4][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[CH2:6][CH2:7][CH2:16][C:17](=[O:20])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 135824294-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol

Product 1

HCID 954956,10-Dimethylundecan-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

4-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol (0.960 g; 5.10-3 mole) is kept at a temperature in the region of 40° C. and protected from light, in the presence of silver trifluoromethanesulphonate (1.285 g; 5.10-3 mole) in a mixture (50 cc) of tetrahydrofuran and water (3:1 by volume). After the reaction mixture has reacted for 20 hours and has been treated under the conditions of Example 1, the raw product obtained is hydrogenated in the presence of palladium on charcoal (5% in hexane). After chromatography on a silica column under reduced pressure with elution with a mixture of ether and petroleum-ether (3:7 by volume), 6,10-dimethylundecan-2-one (0.792 g) is obtained, having the following characteristics:

Workup

  1. customis kept at a temperature in the region of 40° C.
  2. customAfter the reaction mixture has reacted for 20 hours
  3. additionhas been treated under the conditions of Example 1
  4. customthe raw product obtained
  5. washAfter chromatography on a silica column under reduced pressure with elution
  6. additionwith a mixture of ether and petroleum-ether (3:7 by volume)

Sources & evidence

ORD record
ord-2bb160207204494fb94d884b6d086b00
Source dataset
uspto-grants-1985_12
Patent number
US04556742

Reaction notes

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