Sodium Carbonate → Methyl 2-(chloromethyl)pyridine-3-carboxylate

HRID 1799543

反応式

HRID 1799543 の反応式
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].O=P(Cl)(Cl)[Cl:15].C([O-])([O-])=O.[Na+].[Na+]>>[Cl:15][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[Cl:15][CH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 20163965Methyl 2-methylnicotinate 1-oxide

生成物 2

HCID 19081344Methyl 2-(chloromethyl)pyridine-3-carboxylateHCID 59650775Methyl 6-chloro-2-methylpyridine-3-carboxylate

実験手順

Methyl 2-methylpyridine-3-carboxylate 1-oxide (2.93 g, 17.53 mmol) was stirred in refluxing POCl3 (17 mL, 182 mmol) for 3 hours. Room temperature was attained and the reaction mixture poured into ice-water. The resulting dark solution was neutralised with solid Na2CO3 and the mixture was extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (2-30% EtOAc/hexanes) gave methyl 6-chloro-2-methylpyridine-3-carboxylate as a pale yellow oil (A) and methyl 2-(chloromethyl)pyridine-3-carboxylate (B) as an orange oil.

後処理

  1. customRoom temperature
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by silica gel chromatography (2-30% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-22adf6bb81ad4724a884cded33c7e30f
出典データセット
uspto-grants-2013_01
特許番号
US08344144B2

関連ノート

読み込み中…