Triethylamine → 2-(Chloromethyl)-5-phenylpyridine

HRID 1034296ノート

反応式

HRID 1034296 の反応式
[C:1]1([C:7]2[CH:12]=[N+:11]([O-])[C:10]([CH3:14])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:17])=O.CCN(CC)CC>C(Cl)Cl>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:14][Cl:17])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 149805285-Phenyl-2-picoline N-oxide

生成物 1

HCID 146503502-(Chloromethyl)-5-phenylpyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of 75 g 5-phenyl-2-picoline N-oxide from Step 1 in 375 mL of CH2Cl2 were added simultaneously a solution of 41.5 mL phosphoryl chloride in 150 mL of CH2Cl2 and a solution of 62 mL Et3N in 150 mL of CH2Cl2. The rate of addition was adjusted so that the reaction reached reflux temperature. The addition completed, the reaction was poured into a solution of NH4OAc (25%), stirred 30 minutes, and extracted with EtOAc. The organic layer was dried over MgSO4, filtered on a silica gel bed, and evaporated to dryness. The resulting solid was recrystallised from petroleum ether (30°-60° C.) to afford pure title product, m.p.: 73° C. The filtrate was chromatographed on silica gel (hexane/EtOAc 9:1) to give the title product along with 4-chloro-5-phenyl-2-picoline and 6-chloro-5-phenyl-2-picoline.

後処理

  1. additionThe rate of addition
  2. temperaturereached reflux temperature
  3. additionThe addition
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered on a silica gel bed
  7. customevaporated to dryness
  8. customThe resulting solid was recrystallised from petroleum ether (30°-60° C.)

出典と根拠

ORDレコード
ord-b23a72cd77b14c82b135bb03c3dcdeac
出典データセット
uspto-grants-1994_05
特許番号
US05314900

反応ノート

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