Pyridine → Acetic Acid 3-(4-phenoxy-quinazolin-6-yl)-allyl ester

HRID 1264056노트

반응식

HRID 1264056 반응식
[O:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][OH:21])[CH:16]=2)[N:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl.Cl>[O:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][O:21][C:28](=[O:30])[CH3:29])[CH:16]=2)[N:11]=[CH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 694856033-(4-Phenoxy-quinazolin-6-yl)-prop-2-en-1-ol

생성물 1

HCID 69484701Acetic Acid 3-(4-phenoxy-quinazolin-6-yl)-allyl ester

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매2회

실험 절차

To alcohol 25 (900 mg, 3.23 mmol) and pyridine (0.8 mL, 10 mmol) in dry CH2Cl2 (15 mL) at 0° C. was added acetyl chloride (0.3 mL, 4.2 mmol). The resulting mixture was stirred for 2 hours, the diluted with CH2Cl2 (10 mL) and 5% HCl (10 mL). The mixture was transferred to a separatory funnel and the organic layer washed with H2O and brine. The organic layer was dried (Na2SO4), solids filtered and the solvent removed in vacuo to provide the desired acetate 26 as a yellow waxy solid (1.04 g, 100%).1H NMR (CDCl3; 400 MHz): δ: 8.72 (s, 1H), 8.30 (d, 1H, J=1.7 Hz), 7.98 (m, 2H), 7.49 (m, 2H), 7.30 (m, 1H), 7.25 (m, 2H), 6.84 (d, 1H, J=16.0 Hz), 6.46 (m, 1H), 4.79 (dd, 2H, J=6.2 Hz, 1.2 Hz), 2.11 (s, 3H).

후처리

  1. customThe mixture was transferred to a separatory funnel
  2. washthe organic layer washed with H2O and brine
  3. dry with materialThe organic layer was dried (Na2SO4), solids
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-957b8fa3c8f5490c9c8b98e5b1ae2eb2
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541481B2

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