Sodium Iodide → (4-Pentenyl)phosphonic acid diethyl ester

HRID 2214428노트

반응식

HRID 2214428 반응식
[I-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12].ICCCC=C>CC(C)=O>[CH2:11]([O:10][P:9]([CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8])(=[O:16])[O:13][CH2:14][CH3:15])[CH3:12]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 31215Triethyl phosphiteHCID 707041-Pentene, 5-bromo-HCID 109871725-Iodopent-1-ene

생성물 1

HCID 13462469(4-Pentenyl)phosphonic acid diethyl ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Sodium iodide (100.6 g, 0.66 mol, 1.1 eq.) was added to a solution of 1-bromo-4-pentene (100 g, 0.67 mol) in acetone (250 mL) and the mixture was stirred at room temperature overnight. The mixture was filtered and the solid was washed with acetone. The acetone filtrate and the acetone wash were combined. The acetone was then removed by distillation, revealing 1-iodo-4-pentene, which was used in the next step. 1H NMR (CDCl3) δ=5.8 (m, 1H), 5.0 (m, 2H), 3.2 (t, 2H), 2.2 (sq, 2H), 1.8 (sq, 2H). Triethyl phosphite (400 mL, 2.3 mol, 3.5 eq.) was added to the 1-iodo-4-pentene, and the mixture was heated to 130° C. for three hours. Diethyl ethyl phosphonate was removed by fractional vacuum distillation, revealing the desired 4-pentenyl phosphonic acid diethyl ester which was used without further purification. 1H NMR (CDCl3) δ=5.7 (m, 1H), 4.8 (m, 2H), 4.0 (m, 4H), 2.0 (sq, 2H), 1.7 (m, 4H), 1.2 (t, 6H). 31P NMR (CDCl3) δ=33.3.

후처리

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with acetone
  3. washThe acetone filtrate and the acetone wash
  4. customThe acetone was then removed by distillation
  5. temperaturethe mixture was heated to 130° C. for three hours
  6. customDiethyl ethyl phosphonate was removed by fractional vacuum distillation
  7. customwas used without further purification

출처 및 근거

ORD 기록
ord-1d8648c8270d42b6bae731ca0e9a111b
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109184B2

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