Thionyl Chloride → 3-(Chloromethyl)-2-methylpyridine

HRID 1680

反応式

HRID 1680 の反応式
O[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.O=S(Cl)[Cl:12]>C(Cl)Cl>[Cl:12][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 302564(2-Methylpyridin-3-yl)methanol

生成物 1

HCID 122437113-(Chloromethyl)-2-methylpyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 3-hydroxymethyl-2-methylpyridine from Step 1 above (1.00 g, 8.13 mmol) in 40 mL of CH2Cl2 at ambient temperature was added SOCl2 (9.0 mL, 123 mmol). The reaction mixture was stirred for 4 hours, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was washed with additional CH2 Cl2 (2×40 mL). The combined organic layers were evaporated under reduced pressure to give 3-chloromethyl-2-methylpyridine as a pale yellow-brown solid (TLC: Rf =0.85 in 5% MeOH in CH2Cl2 ; FAB MS m/z 142 (M+ +H)).

後処理

  1. customthe solvent and excess SOCl2 were evaporated under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with additional CH2 Cl2 (2×40 mL)
  5. customThe combined organic layers were evaporated under reduced pressure

出典と根拠

ORDレコード
ord-b03b7005ae0f4e16a4358a35620a3d77
出典データセット
uspto-grants-1998_03
特許番号
US05726172

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