Chloroacetone → 7-(2-oxopropoxy)-2H-chromen-2-one

HRID 263957

반응식

HRID 263957 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21](=[O:23])[CH3:22]>CC(C)=O>[O:23]=[C:21]([CH3:22])[CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8](=[O:12])[O:9][C:10]=2[CH:11]=1

참가 물질

5

반응물 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 5281426Umbelliferone

생성물 1

HCID 7665507-(2-oxopropoxy)-2H-chromen-2-one수율 96.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 7-hydroxycoumarin (1.62 g, 10 mmol) in acetone (20 ml) were added potassium carbonate (5.53 g, 40 mmol) and chloroacetone (1.38 g, 15 mmol). The resulting mixture was refluxed for 4 h. (monitored by TLC). Evaporation of the solvent gave a residue which was poured into ice water (50 ml). The resulting solid was collected and crystallized from ethyl acetate to afford 7-(2-oxopropoxy)-2H-1-benzopyran-2-one (3a) (2.10 g, 96.1%) as a white needle crystal. mp: 165°-167° C.; IR(KBr) νmax : 1709, 1620; UV(CHCl3) λmax (log ε): 308 (4.14), 244 (3.52); 1H-NMR (CDCl3): δ2.31 (s, 3H, CH3), 4.65 (s, 2H, OCH2), 6.29 (d, 1H, 3-H), 6.76 (d, 1H, 8-H), 6.88 (dd, 1H, 6-H), 7.42 (d, 1H, 5-H), 7.65 (d, 1H, 4-H). Anal. Calcd for C12H10O4 : C, 66.05; H, 4.62. Found: C, 65.98; H, 4.61.

후처리

  1. temperatureThe resulting mixture was refluxed for 4 h. (monitored by TLC)
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. customThe resulting solid was collected
  5. customcrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-39a40ffeb2974963960c7d5c9d90a143
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646164

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