Phenyl chloroformate → 5-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-4H-pyridine-1,3-dicarboxylic acid 3-ethyl ester 1-phenyl ester

HRID 1475763

반응식

HRID 1475763 반응식
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH:8]=[N:7][CH:6]=1)[CH3:2].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24].[CH2:32]([Mg]Br)[CH3:33]>C1COCC1>[C:26]1([O:25][C:23]([N:7]2[CH:8]=[C:9]([O:11][CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)[CH:10]([CH2:32][CH3:33])[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:21])=[CH:6]2)=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 15891Phenyl chloroformateHCID 671698645-[2-(3-Chloro-phenyl)-ethoxy]-nicotinic Acid Ethyl EsterHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 671712595-[2-(3-Chloro-phenyl)-ethoxy]-4-ethyl-4H-pyridine-1,3-dicarboxylic acid 3-ethyl ester 1-phenyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-30 °C

실험 절차

The compound of step 1 (100 mg, 0.327 mmol) was dissolved in THF (1.5 ml) and the mixture was cooled to −30° C. Phenyl chloroformate (77.6 mg, 0.49 mmol) was added and the mixture was stirred for 10 minutes. Ethyl magnesiumbromide (0.589 ml, 1M in THF) was added at −30° C. and the mixture was stirred for 30 minutes, partitioned between diethylether and aqueous ammonium chloride solution, the combined organic extracts were dried over sodium chloride and evaporated to dryness in vacuo. The raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient to yield the title compound (84 mg).

후처리

  1. stirringthe mixture was stirred for 30 minutes
  2. custompartitioned between diethylether and aqueous ammonium chloride solution
  3. dry with materialthe combined organic extracts were dried over sodium chloride
  4. customevaporated to dryness in vacuo
  5. customThe raw material was purified by silica gel chromatography with a heptane/ethyl acetate gradient

출처 및 근거

ORD 기록
ord-d1301782727445229f960c00152ae8af
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018383B2

연결된 노트

불러오는 중…