Octanoyl chloride → HCID 19885933, compound

HRID 654906Notes

Reaction equation

HRID 654906 reaction equation
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[C:18]([O:21][CH:22]([C:31]1[CH:35]([OH:36])[O:34][C:33](=[O:37])[CH:32]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=[O:20])[CH3:19]>O1CCCC1.O>[C:18]([O:21][CH:22]([C:31]1[CH:35]([O:36][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:34][C:33](=[O:37])[CH:32]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 15663259HCID 15663259, compound

Product 1

HCID 19885933HCID 19885933, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Octanoyl chloride (83.6 μl, 0.49 mmol), followed by triethylamine (68.2 μl, 0.49 mmol), was added to 4-(1-acetoxynonyl)-5-hydroxy-2(5H)-furanone (132.6 mg, 0.47 mmol) in tetrahydrofuran (6 ml) at 0°. Stirring was continued for 14h while the ice bath attained room temperature. The mixture was diluted with water (10 ml) and extracted with dichloromethane. Evaporation of the dried (magnesium sulfate) extract gave a yellow oil, which was flash chromatographed on silica using 30% ethyl ether/petroleum ether. Fractions with Rf 0.38 on evaporation gave the title compound as a colorless oil.

Workup

  1. customattained room temperature
  2. extractionextracted with dichloromethane
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. extractionextract
  6. customgave a yellow oil, which
  7. customchromatographed on silica using 30% ethyl ether/petroleum ether
  8. customFractions with Rf 0.38 on evaporation

Sources & evidence

ORD record
ord-e37c76ea74a34f6489147d8c01df4a7c
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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