Hydrochloric Acid → methyl (2-oxopropoxy)acetate

HRID 635976ノート

反応式

HRID 635976 の反応式
C[Zn]C.[C:4]1(C)C=CC=CC=1.Cl[C:12]([CH2:14][O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:13].Cl>[Cl-].[Na+].O.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[O:13]=[C:12]([CH3:4])[CH2:14][O:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 12361282Methyl (2-chloro-2-oxoethoxy)acetateHCID 178477796HCID 178477796、化合物

生成物 1

HCID 11701055methyl (2-oxopropoxy)acetate収率 84.7%

試薬・触媒・溶媒 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)触媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

A solution of 2M dimethyl zinc in toluene (21 mL, 42 mmol) was cooled to 0° C. under nitrogen, treated with trans-benzyl(chloro)bis(triphenylphosphine)palladium(II) (0.57 g, 76 mmol), treated with methyl 2-(chloroformylmethoxy)acetate (12.6 g, 76 mmol) dropwise over 0.5 hours, stirred for 0.5 hours at 0° C., stirred for 16 hours at ambient temperature, treated with 1M HCl (40 mL) and then brine (20 mL). The organic layer was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography over silica gel (1:2 ethyl acetate/hexanes) to provide the title compound (5.2 g).

後処理

  1. stirringstirred for 16 hours at ambient temperature
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography over silica gel (1:2 ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-51f80755275f44c8b612c5f75ade9500
出典データセット
uspto-grants-2001_02
特許番号
US06191140B1

反応ノート

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