1-Propanol → HCID 12521033, compound

HRID 1734986Notes

Reaction equation

HRID 1734986 reaction equation
[P:1](Cl)([Cl:6])([O:3][CH2:4][CH3:5])=[S:2].[O-:8][CH2:9][CH2:10][CH3:11].[Na+].C(O)CC>O1CCCC1>[P:1]([Cl:6])([O:8][CH2:9][CH2:10][CH3:11])([O:3][CH2:4][CH3:5])=[S:2]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 73907Phosphorodichloridothioic acid, O-ethyl esterHCID 236693631-Propanol, sodium salt (1:1)

Product 1

HCID 12521033HCID 12521033, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 30 g (167 mmole) of O-ethyl dichlorothiophosphate in 100 ml of tetrahydrofuran (THF) and cooled to -70° C. was added a solution of sodium propoxide (from 7.4 g of 60% NaH (184 mmole) and 11 g (176 mmole) of 1-propanol) in 50 ml of THF. After warming to room temperature over 2 hours, the THF was removed in vacuo and the residue was partitioned between 50 ml diethyl ether, 50 ml hexanes, and 25 ml cold water. The organic layer was dried over magnesium sulfate, concentrated in vacuo, and distilled (bp 45°-50 20 C. 1 torr) yielding 20 g of the title compound, an oil. nmr 1.0 t 3H, 1.4 t 3H, 1.8 sextet 2H, 4.4M 4H.

Workup

  1. customthe THF was removed in vacuo
  2. customthe residue was partitioned between 50 ml diethyl ether, 50 ml hexanes, and 25 ml cold water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. distillationdistilled (bp 45°-50 20 C. 1 torr)

Sources & evidence

ORD record
ord-0a56f19b36e34a869ed5c6185156d8e7
Source dataset
uspto-grants-1996_07
Patent number
US05536710

Reaction notes

Loading…