Ethyl chloroacetate → Ethyl 4-chlorobenzofuran-2-carboxylate

HRID 1471670노트

반응식

HRID 1471670 반응식
Cl[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[C:10]=1[CH:11]=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:8][C:9]1[C:10]2[CH:11]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:17][C:13]=2[CH:14]=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 5283932-Chloro-6-hydroxybenzaldehyde

생성물 1

HCID 67983046Ethyl 4-chlorobenzofuran-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl chloroacetate (8.0 mL, 1.3 eq.) was added to a mixture of 2-chloro-6-hydroxy-benzaldehyde (Example 1a), 9.0 g, 57 mmol) and potassium carbonate (16.0 g, 114 mmol) in DMF (100 mL) at rt. The reaction mixture was heated at +120° C. for 1.5 h, cooled to room temperature and filtered through a short bed of Celite. The filtrate was acidified to pH 2 with 5 M HCl and the solution was extracted with dichloromethane (2×100 mL). The combined organic extracts was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography by using hexane/ethyl acetate (9/1) as eluent to give the title compound. Yield: 10 g (77%). 1H NMR (400 MHz, CDCl3) δ ppm 1.44 (t, 3H) 4.56 (q, 2H) 7.29-7.32 (m, 1H) 7.35-7.40 (m, 1H) 7.49-7.52 (m, 1H) 7.60 (s, 1H).

후처리

  1. temperatureThe reaction mixture was heated at +120° C. for 1.5 h
  2. filtrationfiltered through a short bed of Celite
  3. extractionthe solution was extracted with dichloromethane (2×100 mL)
  4. washThe combined organic extracts was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-48ab40ca001b4e55a13d2c4e9e940907
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012457B2

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