Pyridine → HCID 58234695, 화합물

HRID 68249

반응식

HRID 68249 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].N1C=CC=CC=1.Cl[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20]>C1(C)C=CC=CC=1.C(Cl)Cl.O>[C:19](=[O:20])([O:21][CH:22]([CH3:24])[CH3:23])[O:10][C:8]1[CH:9]=[C:2]([Cl:1])[C:3]([CH:4]=[O:5])=[C:6]([Cl:11])[CH:7]=1

참가 물질

7

반응물 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

생성물 1

HCID 58234695HCID 58234695, 화합물수율 81%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

To a 250 mL dry round bottom flask were added 2,6-dichloro-4-hydroxybenzaldehyde (5.73 g, 30.0 mmol), anhydrous CH2Cl2 (30 mL) and pyridine (3.0 mL, 36.5 mmol). The mixture was stirred in an ice-water bath, then a solution of isopropyl chloroformate in toluene (1.0 M, 33.4 mL) was added. After stirring at 0° C. for 2 hours, water (100 mL) and CH2Cl2 (50 mL) were added to the reaction mixture. The CH2Cl2 layer was separated, and the aqueous layer was extracted continually with CH2Cl2 (40 mL×3). The combined CH2Cl2 solution was dried over Na2SO4. After removal of the solvent, the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting) to give 3,5-dichloro-4-formylphenyl isopropyl carbonate (6.72 g) as a colorless oil. Yield: 81%. 1H NMR (CDCl3, 300 MHz): δ=10.53 (s, 1H), 7.41 (s, 2H), 5.09 (seventet, J=6.3 Hz, 1H), 1.48 (d, J=6.3 Hz, 6H). 13C NMR (CDCl3, 75.5 MHz): δ=187.8, 153.8, 151.5, 138.0, 127.8, 122.8, 74.6, 21.8.

후처리

  1. customTo a 250 mL dry round bottom flask
  2. stirringAfter stirring at 0° C. for 2 hours
  3. customThe CH2Cl2 layer was separated
  4. extractionthe aqueous layer was extracted continually with CH2Cl2 (40 mL×3)
  5. dry with materialThe combined CH2Cl2 solution was dried over Na2SO4
  6. customAfter removal of the solvent
  7. customthe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

출처 및 근거

ORD 기록
ord-e295cff8174d4ffc905d584f27a8bf1c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822435B2

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