1,2-Dibromoethane → (2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

HRID 639045

反応式

HRID 639045 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[NH:13][CH:14]=1)[C:2]1C=CC=CC=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].BrCCBr>O.[Pd].CN(C)C=O>[O:17]1[C:10]2[CH:11]=[C:12]([CH2:15][OH:16])[N:13]=[CH:14][C:9]=2[O:8][CH2:1][CH2:2]1

参加物

8

反応物 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

生成物 1

HCID 21873770(2,3-Dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)methanol

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A solution of 5-Benzyloxy-2-hydroxymethyl-1H-pyridin-4-one (2 g, 8.7 mmol) in water (220 mL) containing sodium hydroxide (17 mmol) was hydrogenated over 10% palladium on charcoal (1 g) for 4 hours. The mixture was filtered and evaporated to give a white solid. This solid was dissolved in N,N-dimethylformamide (8 mL) then treated with potassium carbonate (2.9 g) and 1,2-dibromoethane (0.6 mL, 7 mmol). The mixture was heated at 85° C. overnight. The cooled mixture was evaporated onto silica and chromatographed eluting with 10-30% methanol in ethyl acetate affording a white solid (250 mg, 21%); MS (APCl+) m/z 168 (MH+).

後処理

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customto give a white solid
  4. customThe cooled mixture was evaporated onto silica
  5. customchromatographed
  6. washeluting with 10-30% methanol in ethyl acetate affording a white solid (250 mg, 21%)

出典と根拠

ORDレコード
ord-7e03b8c7a8094f4ca56b53ceea538794
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

関連ノート

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