Pyridine → 1-{[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide

HRID 1258582ノート

反応式

HRID 1258582 の反応式
S(Br)([Br:3])=O.[O:5]1[CH2:9][CH2:8][O:7][CH:6]1[C:10]1[N:15]=[C:14]([CH2:16]O)[CH:13]=[CH:12][CH:11]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[BrH:3].[Br-:3].[O:7]1[CH2:8][CH2:9][O:5][CH:6]1[C:10]1[N:15]=[C:14]([CH2:16][N+:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 19361733[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methanol

生成物 1

HCID 671882711-{[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide収率 193.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution thionyl bromide (8.36 g, 40.23 mmol, 1 eq.) in 300 ml dry DCM, cooled to 5° C., was added dropwise a solution of [6-(1,3-dioxolan-2-yl)pyridin-2-yl]methanol (8.1 g, 40.23 mmol, 1 eq.) and pyridine (3.18 g, 40.23 mmol, 1 eq.) in 15 ml dry DCM. On complete addition, the cooling bath was removed, the reaction warmed to room temperature and stirred overnight. 150 ml of water and 150 ml of DCM were added and stirring allowed for 2 mins. The organic layer was separated, dried over MgSO4 and concentrated to give 1-{[6-(1,3-dioxolan-2-yl)pyridin-2-yl]methyl}pyridinium bromide hydrobromide (15.7 g, 96% yield) as a white solid.

後処理

  1. additionOn complete addition
  2. customthe cooling bath was removed
  3. addition150 ml of water and 150 ml of DCM were added
  4. stirringstirring
  5. waitallowed for 2 mins
  6. customThe organic layer was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c6d900cf4c1d46c98f0742e95c39f59b
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

反応ノート

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