Malonic Acid → (E)-10-heptyloxy-dec-3-enoic acid

HRID 1779187Notes

Reaction equation

HRID 1779187 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.C(O)(=O)[CH2:26][C:27]([OH:29])=[O:28].P([O-])(O)(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]/[CH2:26][C:27]([OH:29])=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

8

Reactant 4

HCID 867Malonic AcidHCID 8471TriethylamineHCID 23672064Monosodium phosphateHCID 900601478-Heptyloxy-octanal

Product 1

HCID 90060136(E)-10-heptyloxy-dec-3-enoic acidYield 100.4%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, 8-heptyloxy-octanal (178.0 mg, 0.734 mmol) obtained in Step D-2 was dissolved in toluene (3.56 mL), and triethylamine (184 μL, 1.32 mmol) and a solution of malonic acid (137.6 mg, 1.32 mmol) in DMF (0.178 mL) were added in order at 75° C. The mixture was stirred at 90° C. for 16 hours. After cooling to room temperature, an aqueous solution (2.6 mL) of 30% sodium dihydrogen phosphate and ethyl acetate (5.2 mL) were added, and the mixture was stirred at room temperature for 5 minutes. After extraction, the organic layer was washed with water. The aqueous layer was washed with ethyl acetate. The combined organic layer was then washed again with water and a saturated brine, dried over anhydrous sodium sulfate, and then filtered. The solvent was distilled off to obtain 209.7 mg (quant.) of (E)-10-heptyloxy-dec-3-enoic acid (ESI (LC/MS positive mode) m/z 285 (M+H); Rt 2.23 min.)

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture was stirred at room temperature for 5 minutes
  3. extractionAfter extraction
  4. washthe organic layer was washed with water
  5. washThe aqueous layer was washed with ethyl acetate
  6. washThe combined organic layer was then washed again with water
  7. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-156c8fdae8a240ebaac208d542079bab
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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