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

HRID 850158

反応式

HRID 850158 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-db5f8688c1a342a2b271f64fbfe5a352
出典データセット
uspto-grants-2000_01
特許番号
US06015905

関連ノート

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