Tetrahydrofuran → (5Z)-3-methylnon-5-enyl acetate

HRID 1799151Notes

Reaction equation

HRID 1799151 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:10][CH2:11][CH2:12][CH:13]([CH3:17])[CH2:14][CH:15]=O)(=[O:9])[CH3:8].[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[C:7]([O:10][CH2:11][CH2:12][CH:13]([CH3:17])[CH2:14]/[CH:15]=[CH:22]\[CH2:18][CH2:19][CH3:20])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 110519253-Methyl-5-oxopentyl acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86625206(5Z)-3-methylnon-5-enyl acetateYield 78%

Reagents, catalysts & solvents 1

HCID 159628Butyltriphenylphosphonium bromideCatalyst

Procedure

Under an atmosphere of nitrogen, a solution of 46.3 g (413 mmol) of potassium tert-butoxide in 250 mL of dry THF was a added between −15° C. and −10° C. to a stirred mixture of 150 g (376 mmol) butyl triphenylphosphonium bromide in 500 mL of dry THF. After complete addition, stirring was continued at −10° C. for 30 min, prior to the dropwise addition of 65.3 g (413 mmol) of 3-methyl-5-oxopentyl acetate in 250 mL of dry THF within a period of 30 min. Stirring was continued a further 15 min at −10° C., before the cooling bath was removed and the reaction mixture was allowed to warm to room temp. After 3 h of stirring at room temp., the reaction mixture was poured into 1 L of water, the organic layer separated and aqueous one extracted twice with 1 L of ether each. The combined organic extracts were washed with water and brine, dried with sodium sulphate, and concentrated under reduced pressure. The crude material (191 g) was purified by flash chromatography (1.00 kg of silica gel, pentane/ether, 19:1, Rf=0.40) to afford 57.9 g (78%) of (5Z)-3-methylnon-5-enyl acetate as a colourless liquid.

Workup

  1. additionAfter complete addition
  2. stirringStirring
  3. waitwas continued a further 15 min at −10° C., before the cooling bath
  4. customwas removed
  5. stirringAfter 3 h of stirring at room temp.
  6. additionthe reaction mixture was poured into 1 L of water
  7. customthe organic layer separated
  8. extractionaqueous one extracted twice with 1 L of ether each
  9. washThe combined organic extracts were washed with water and brine
  10. dry with materialdried with sodium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customThe crude material (191 g) was purified by flash chromatography (1.00 kg of silica gel, pentane/ether, 19:1, Rf=0.40)

Sources & evidence

ORD record
ord-f9b6acbd9dc444dd9cba7d90835ee07d
Source dataset
uspto-grants-2013_01
Patent number
US08344023B2

Reaction notes

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