Hydrochloric Acid → Dimethyl [2-oxo-3-(pyrid-3-yloxy)propyl]phosphonate

HRID 1579493노트

반응식

HRID 1579493 반응식
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](OCC)=[O:22])[CH:14]=1.Cl>CCCCCC.O1CCCC1>[O:22]=[C:21]([CH2:20][O:19][C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 12958Dimethyl methylphosphonateHCID 4763754Ethyl 2-(pyridin-3-yloxy)acetateHCID 178418339Butyllithium

생성물 1

HCID 53690992Dimethyl [2-oxo-3-(pyrid-3-yloxy)propyl]phosphonate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

n-Butyl-lithium (4.76ml. of a 2.1M solution in hexane) was added to a solution of dimethyl methylphosphonate (1.24g.) in dry tetrahydrofuran at -78°C. in an atmosphere of nitrogen. After 10 minutes, a solution of ethyl 3-pyridyloxyacetate (0.90g.) in dry tetrahydrofuran (5ml.) was added dropwise, and the mixture was stirred for 1 hour at -78°C. The reaction mixture was taken to pH 1-2 with 2N hydrochloric acid and the solvents were removed under reduced pressure. The residue was shaken with water (10ml.) and extracted with ether (3 × 10ml.). The extracts were discarded, and the aqueous solution was adjusted to pH 7-8 with sodium bicarbonate solution and extracted with chloroform (6 × 10ml.). The combined extracts were evaporated, to give dimethyl [2-oxo-3-(pyrid-3-yloxy)propyl]phosphonate as an oil, RF = 0.2 (10% methanol in ethyl acetate).

후처리

  1. customthe solvents were removed under reduced pressure
  2. stirringThe residue was shaken with water (10ml.)
  3. extractionextracted with ether (3 × 10ml.)
  4. extractionextracted with chloroform (6 × 10ml.)
  5. customThe combined extracts were evaporated

출처 및 근거

ORD 기록
ord-2ebfd4cf032c498d983ff7164b80295a
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03931206

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