Dimethylformamide → 2-[2-(2,5-Dimethylphenoxymethyl)-alpha-methoxybenzyl]pyridine

HRID 2268753ノート

反応式

HRID 2268753 の反応式
[CH3:1][C:2]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:3]=1[O:4][CH2:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[OH:9].[CH3:25]N(C)C=O.CI.[H-].[Na+]>CCOCC>[CH3:1][C:2]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:3]=1[O:4][CH2:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[O:9][CH3:25]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 155451342-[2-(2,5-Dimethylphenoxymethyl)-alpha-hydroxybenzyl]pyridine

生成物 1

HCID 155451352-[2-(2,5-Dimethylphenoxymethyl)-alpha-methoxybenzyl]pyridine収率 92.3%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a mixture of 0.42 g (1.3 mmol) of 2-[2-(2,5-dimethylphenoxymethyl)-α-hydroxybenzyl]pyridine, 4 ml of N,N-dimethylformamide and 0.12 ml (2 mmol) of methyl iodide was added 0.07 g (1.7 mmol) of 60% sodium hydride under ice-cooling and stirred at the same temperature for 3 hours. After completion of the reaction, 100 ml of ether was added and washed twice with 80 ml of brine. The ether layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2-[2-(2,5-dimethylphenoxymethyl)-α-methoxybenzyl]pyridine (0.40 g, 92.3%) as colorless oil.

後処理

  1. temperaturecooling
  2. additionwas added
  3. washwashed twice with 80 ml of brine
  4. dry with materialThe ether layer was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

出典と根拠

ORDレコード
ord-1509afb2056647439fc8c4d2697a2385
出典データセット
uspto-grants-2001_12
特許番号
US06329371B1

反応ノート

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