Water → HCID 56612223, compound

HRID 637570Notes

Reaction equation

HRID 637570 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.[O:15]1[CH2:19][CH2:18]CC1.O.[C:21](=O)(O)[O-].[Na+]>C(OCC)C.FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:9][C:5](=[CH:4][CH:10]=[CH:11][CH:12]([CH3:13])[CH3:14])[CH2:6][CH:7]=[CH:21][C:19](=[O:15])[CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 135824294-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol

Product 1

HCID 56612223HCID 56612223, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 3283Diethyl EtherSolvent

Procedure

4-Isopropenyl-3,7-dimethyl-6-octen-1-yn-3-ol (0.192 g; 10-3 mole) is kept at a temperature in the region of 40° C. and protected from light in the presence of silver trifluoromethanesulphonate (0.257 g; 10-3 mole) in a mixture (3:1 by volume) of tetrahydrofuran and water (10 cc). After 20 hours the reaction mixture is diluted with ethyl ether (20 cc) and treated with a saturated solution of sodium bicarbonate (5 cc). After separation, the organic phase is washed with demineralised water until neutral, and then dried over magnesium sulphate. After filtration, evaporation of the solvent under reduced pressure (20 mm Hg; 2.7 kPa) and purification by chromatography on alumina, 6,10-dimethyl-3,6,8-undecatrien-2-one (0.110 g) is obtained in a yield of 57%, having the following characteristics:

Workup

  1. customis kept at a temperature in the region of 40° C.
  2. customAfter separation
  3. washthe organic phase is washed with demineralised water until neutral, and
  4. dry with materialthen dried over magnesium sulphate
  5. filtrationAfter filtration, evaporation of the solvent
  6. customunder reduced pressure (20 mm Hg; 2.7 kPa) and purification by chromatography on alumina

Sources & evidence

ORD record
ord-84215a0746a24dd3b2f2ec2219325290
Source dataset
uspto-grants-1985_12
Patent number
US04556742

Reaction notes

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