Chloromethyl Methyl Ether → 1-[3-(tert-Butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanone

HRID 1295993ノート

反応式

HRID 1295993 の反応式
C(N(C(C)C)CC)(C)C.[C:10]([C:14]1[CH:15]=[C:16]([C:24](=[O:26])[CH3:25])[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[C:19]=1[OH:20])([CH3:13])([CH3:12])[CH3:11].[CH3:27][O:28][CH2:29]Cl>O1CCCC1>[C:10]([C:14]1[CH:15]=[C:16]([C:24](=[O:26])[CH3:25])[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[C:19]=1[O:20][CH2:27][O:28][CH3:29])([CH3:13])([CH3:11])[CH3:12]

参加物

5

反応物 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 229297281-[3-(Tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone

生成物 1

HCID 589099361-[3-(tert-Butyl)-4-(methoxymethoxy)-5-nitrophenyl]-1-ethanone収率 99.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diisopropylethylamine (65 ml, 373 mmol) was added to a solution of 1-[3-(tert-butyl)-4-hydroxy-5-nitrophenyl]-1-ethanone (58.6 g, 247 mmol) in tetrahydrofuran (350 ml) under a nitrogen atmosphere while cooling on ice, and then chloromethyl methyl ether (24.5 ml, 322 mmol) was added dropwise. After stirring at the same temperature for 30 minutes, ice water (250 ml) was added and extraction was performed twice with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid water, water, saturated aqueous sodium hydrogencarbonate and brine in that order. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure to yield the title compound (69.4 g, 99.9% yield) as a light brown oil. This was used without purification for the following reaction.

後処理

  1. temperaturewhile cooling on ice
  2. extractionextraction
  3. washThe organic layer was washed with 1 N hydrochloric acid water, water, saturated aqueous sodium hydrogencarbonate and brine in that order
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-6f94ca097aa34d8099120646fbf80039
出典データセット
uspto-grants-2007_07
特許番号
US07244730B2

反応ノート

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