Dabco → Ethanethioic acid, S-[(diphenylphosphino)methyl] ester

HRID 488893Notes

Reaction equation

HRID 488893 reaction equation
B.[C:2]1([P:8]([CH2:15][S:16][C:17](=[O:19])[CH3:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N2CCN(CC2)C1>C1(C)C=CC=CC=1>[C:2]1([P:8]([CH2:15][S:16][C:17](=[O:19])[CH3:18])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9237DabcoHCID 178419194HCID 178419194, compound

Product 1

HCID 11266196Ethanethioic acid, S-[(diphenylphosphino)methyl] esterYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Compound 10b (4.00 g, 13.9 mmol) was dissolved in toluene (0.14 L) under Ar(g). DABCO (1.56 g, 13.9 mmol) was added, and the mixture was heated at 40° C. for 4 h. Solvent was removed under reduced pressure, and the residue was dissolved in CH2Cl2 and washed with both 1 N HCl and saturated brine. The organic layer was dried over MgSO4(s), and the solvent was removed under reduced pressure. Compound 11b was isolated in 95% yield, and was used without further purification. Spectral Data. As reported previously.4b

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with both 1 N HCl and saturated brine
  4. dry with materialThe organic layer was dried over MgSO4(s)
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-75433dfef7c549668436ed6dc735f151
Source dataset
uspto-grants-2005_12
Patent number
US06974884B2

Reaction notes

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