Hydrochloric Acid → HCID 86651762, compound

HRID 1945172Notes

Reaction equation

HRID 1945172 reaction equation
Cl.[CH:2]1([P:8]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([S:16]([O-:19])(=[O:18])=[O:17])[CH2:11]2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Na+].[CH2:27](O)[CH3:28]>>[CH:20]1([P:8]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([S:16]([O:19][CH2:27][CH3:28])(=[O:18])=[O:17])[CH2:11]2)=[O:9])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86651763HCID 86651763, compound

Product 1

HCID 86651762HCID 86651762, compound

Procedure

Hydrochloric acid (0.7 g; 38 wt. % solution) is added to DCHPOCHS-Na (1.5 g; 3.8 mmoL) in ethanol (20 mL), and the mixture is stirred for 30 minutes. Then, the ethanol is evaporated, and the residue is dried in vacuum. Dichloromethane (20 mL) and triethylorthoacetate (1.85 g; 11.4 mmoL) are added to the residue, and the resulting mixture is stirred under reflux for 10 hours. The mixture is then washed with saturated sodium bicarbonate (15 mL), then water, and then dried with sodium sulfate. The organic solvent and excess reagent are removed. The residue obtained therefrom is dried in vacuum for 1 hour to yield Ethyl 3-(dicyclohexylphosphinyl)-cyclohexane-1-sulfonate (DCHPOCHS-Et). Yield: 1.36 g (89%) 31P{1H} NMR(C6D6, ppm): 51.28 (major) and 49.24 (minor).

Workup

  1. customThen, the ethanol is evaporated
  2. customthe residue is dried in vacuum
  3. additionDichloromethane (20 mL) and triethylorthoacetate (1.85 g; 11.4 mmoL) are added to the residue
  4. stirringthe resulting mixture is stirred
  5. temperatureunder reflux for 10 hours
  6. washThe mixture is then washed with saturated sodium bicarbonate (15 mL)
  7. dry with materialwater, and then dried with sodium sulfate
  8. customThe organic solvent and excess reagent are removed
  9. customThe residue obtained
  10. customtherefrom is dried in vacuum for 1 hour

Sources & evidence

ORD record
ord-5825a4f6c0c54cca937dcc1e7c92adf0
Source dataset
uspto-grants-2013_03
Patent number
US08394978B2

Reaction notes

Loading…