Water → (E)-methyl 2-[2-(6-bromopyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate

HRID 850158

반응식

HRID 850158 반응식
C[O-].[Na+].[CH:4]([O:6][CH3:7])=[O:5].[Br:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][C:24](OC)=[O:25])[CH:12]=[CH:11][CH:10]=1.O>C1(C)C=CC=CC=1>[Br:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2/[C:23](=[CH:24]\[OH:25])/[C:4]([O:6][CH3:7])=[O:5])[CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7865Methyl formateHCID 10942334Sodium MethoxideHCID 19366333Methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate

생성물 1

HCID 19366331(E)-methyl 2-[2-(6-bromopyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate수율 97.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Sodium methoxide (0.34 g, 6.0 mmol) and methyl formate (1 ml, 16 mmol) were added portionwise to a stirred solution of methyl 2-(6-bromopyrid-2-yloxymethyl)phenylacetate (0.8 g, 2.3 mmol) in dry toluene (10 ml) under a nitrogen atmosphere at room temperature. After 8 hours at room temperature the mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were washed with water, dried and the ethyl acetate removed to give (E)-methyl 2-[2-(6-bromopyrid-2-yloxymethyl)phenyl]-3-hydroxyacrylate (0.82 g, 80%) as a brown gum which was used in the final stage without further purification; 1H NMR (270 MHz)δ: 3.74(3H,s), 5.28(2H,s), 6.66(1H,d), 7.06(1H,d), 7.15-7.55(6H,m), 11.95(1H,d) ppm.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were washed with water
  3. customdried
  4. customthe ethyl acetate removed

출처 및 근거

ORD 기록
ord-db5f8688c1a342a2b271f64fbfe5a352
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06015905

연결된 노트

불러오는 중…