Diethyl Ether → Methyl cis-5-(11-tetradecenyloxy)-2-furyl ketone

HRID 649226

Reaction equation

HRID 649226 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=O)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14].[CH3:24]COCC.C[Li].[Cl-].[NH4+]>C(O)(=O)C>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([CH3:24])=[O:23])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 13655994cis-5-(11-Tetradecenyloxy)furancarboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 13655996Methyl cis-5-(11-tetradecenyloxy)-2-furyl ketone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.2 g (0.013 mole) of cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid and 50 ml of anhydrous ether was stirred at room temperature and 20.2 ml (0.0313 mole) of methyllithium (1.55 molar in hexane) added over 15 minutes. The mixture was stirred at room temperature for 3 hours and poured into saturated ammonium chloride solution. About 10 ml of glacial acetic acid was added and the phases separated. The ether layer was washed with water and evaporated to dryness to give a light yellow semisolid residue which was recrystallized twice from methanol to give methyl cis-5-(11-tetradecenyloxy)-2-furyl ketone, M.P. 3638° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. customthe phases separated
  3. washThe ether layer was washed with water
  4. customevaporated to dryness
  5. customto give a light yellow semisolid residue which
  6. customwas recrystallized twice from methanol

Sources & evidence

ORD record
ord-868fae1ecd7740ab9c5c90e051fa1a9d
Source dataset
uspto-grants-1988_04
Patent number
US04738984

Linked notes

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