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

HRID 2214428ノート

反応式

HRID 2214428 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 13462469(4-Pentenyl)phosphonic acid diethyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1d8648c8270d42b6bae731ca0e9a111b
出典データセット
uspto-grants-2006_09
特許番号
US07109184B2

反応ノート

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