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

HRID 128706

반응식

HRID 128706 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-561e0249275f4c94b431010641f51009
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464855

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