Water → HCID 90060170, compound

HRID 1779145Notes

Reaction equation

HRID 1779145 reaction equation
O=[C:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH2:21]([SH:24])[CH2:22][SH:23].O>ClCCl>[CH2:14]([C:2]1([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[S:24][CH2:21][CH2:22][S:23]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 109021,2-EthanedithiolHCID 15569759Methyl 9-oxo-hexadecanoate

Product 1

HCID 90060170HCID 90060170, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, methyl 9-oxo-hexadecanoate (No. 4984860; 2.39 g, 8.40 mmol) was dissolved in dichloromethane (47 mL), and the solution was cooled to 0° C. While maintaining the temperature at 0° C., 1,2-ethanedithiol (840 μL, 10.1 mmol), and borontrifluoride-ethylether complex (1.24 mL, 10.1 mmol) were sequentially added, and the mixture was stirred at 0° C. for 5 minutes and at room temperature for 2 hours. Water was added to the reaction solution to stop the reaction, and the solution was extracted with dichloromethane. The organic layer was sequentially washed with a saturated sodium bicarbonate aqueous solution and a saturated brine, and dried over anhydrous sodium sulfate. After the organic layer was filtered and the solvent was distilled off, the resulting residue was purified with SP1 (SiO2 cartridge, 5.0% ethyl acetate/n-hexane, Rf=0.5) to obtain methyl 8-(2-heptyl-[1,3]dithiolan-2-yl)-octanoate (No. 5553355; 2.57 g, 85% yield).

Workup

  1. temperatureWhile maintaining the temperature at 0° C.
  2. customthe reaction
  3. extractionthe solution was extracted with dichloromethane
  4. washThe organic layer was sequentially washed with a saturated sodium bicarbonate aqueous solution
  5. dry with materiala saturated brine, and dried over anhydrous sodium sulfate
  6. filtrationAfter the organic layer was filtered
  7. distillationthe solvent was distilled off
  8. customthe resulting residue was purified with SP1 (SiO2 cartridge, 5.0% ethyl acetate/n-hexane, Rf=0.5)

Sources & evidence

ORD record
ord-827887742f5c4683b3cd13657cc30769
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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