Triethylamine → 4-[(Diphenoxyphosphinyl)oxy]-2,5-dihydro-3-thiophenecarboxylic acid methyl ester

HRID 128706

Reaction equation

HRID 128706 reaction equation
[C:1]([CH:5]1[C:9](=[O:10])[CH2:8][S:7][CH2:6]1)([O:3][CH3:4])=[O:2].C(N(CC)CC)C.[C:18]1([O:24][P:25](Cl)([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:4][O:3][C:1]([C:5]1[CH2:6][S:7][CH2:8][C:9]=1[O:10][P:25]([O:24][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([O:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:26])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester

Product 1

HCID 536975314-[(Diphenoxyphosphinyl)oxy]-2,5-dihydro-3-thiophenecarboxylic acid methyl esterYield 108.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-carbomethoxytetrahydrothiophene-4-one (Gianturco M. A., Friedel P., Giammarino A. S., Tetrahedron, 20:1772 (1964)) (4.0 g, 25 mmol) and triethylamine (6.6 g, 65 mmol) in 50 mL dry THF at 0° was added, over a 15 minute period, diphenylchlorophosphate (17.5 g, 65 mmol). The reaction mixture was stirred at room temperature for 2 days, then treated with ice-cold water and extracted with diethyl ether. The extracts were washed with saturated NaHCO3, brine, dried with Na2SO4, and evaporated to yield an oil (10.6 g).

Workup

  1. additiontreated with ice-cold water
  2. extractionextracted with diethyl ether
  3. washThe extracts were washed with saturated NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-561e0249275f4c94b431010641f51009
Source dataset
uspto-grants-1995_11
Patent number
US05464855

Linked notes

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