Hydrochloric Acid → methyl (2-oxopropoxy)acetate

HRID 478267노트

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HRID 478267 반응식
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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 12361282Methyl (2-chloro-2-oxoethoxy)acetateHCID 178477796HCID 178477796, 화합물

생성물 1

HCID 11701055methyl (2-oxopropoxy)acetate수율 84.7%

시약·촉매·용매 2

HCID 11007180Palladium(2+) chloride phenylmethanide--triphenylphosphane (1/1/1/2)촉매HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ae459b97dd7f46e3aa91d48415cb38c9
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642222B2

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