Methoxymethyl-triphenylphosphonium chloride → 4-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine

HRID 1061441ノート

反応式

HRID 1061441 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1([Li])C=CC=CC=1.[Cl:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38]([CH:40]2[CH2:42][CH2:41]2)=O)[C:33]=1[O:43][CH3:44]>CCOCC>[Cl:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38]([CH:40]2[CH2:42][CH2:41]2)=[CH:2][O:3][CH3:4])[C:33]=1[O:43][CH3:44]

参加物

5

反応物 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 68297313(4-Chloro-3-methoxy-2-pyridyl)cyclopropylketoneHCID 178506676HCID 178506676、化合物

生成物 1

HCID 682971814-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine収率 43.6%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

30.78 g of (methoxymethyl) triphenyl phosphonium chloride is suspended in 300 ml of anhydrous ether and 102 ml of phenyllithium (0.88 M) was dropped thereto and the resulting mixture was stirred at a room temperature for 15 minutes. 210 ml of ether solution of 18.10 g of (4-chloro-3-methoxy-2-pyridyl)cyclopropylketone (X) was dropped thereto and was stirred at a room temperature for 12 hours. The resulting residue was separated by filtering and washed with ether, and thereafter, the ether filtrate and ether used for washing were collected together and the collected solution was washed with water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 8.94 g of 2-(4-chloro-3-methoxy-2-pyridyl)-2-cyclopropyl-1-methoxyethene (XI).

後処理

  1. stirringwas stirred at a room temperature for 12 hours
  2. customThe resulting residue was separated
  3. filtrationby filtering
  4. washwashed with ether
  5. washfor washing
  6. customwere collected together
  7. washthe collected solution was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-1a4f7689f0364a97b7a3774d422f6bd1
出典データセット
uspto-grants-2003_02
特許番号
US06525066B2

反応ノート

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