p-Toluenesulfonic acid → 3-Bromo-4-(dimethoxymethyl)pyridine

HRID 2383878

反応式

HRID 2383878 の反応式
[CH3:1]C1C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]=[O:20].[CH2:21]([O:23]C(=O)C)C>CO.CCCCCC>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]([O:23][CH3:21])[O:20][CH3:1]

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 27629973-Bromopyridine-4-carboxaldehyde

生成物 1

HCID 207151453-Bromo-4-(dimethoxymethyl)pyridine収率 93.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

PTSA (834 mg, 4.384 mmol) was added to a solution of 3-bromo-pyridine-4-carbaldehyde (600 mg, 3.2256 mmol) in methanol (20 mL). The resulting mixture was heated to reflux for 4 hours. The reaction was monitored by TLC (20% ethylacetate in hexane). The reaction mixture was concentrated and basified with NaHCO3 solution. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine solution, dried over Na7SO4, filtered and the filtrate was concentrated to afford 700 mg of 3-Bromo-4-dimethoxymethyl-pyridine (93.5% yield).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated
  4. customThe reaction mixture was partitioned between water and DCM
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over Na7SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-dc9876e63f714f2a887add182191f39e
出典データセット
uspto-grants-2012_09
特許番号
US08263635B2

関連ノート

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