tert-Butanol → Tert-butyl 3-iodo-2-methoxybenzoate

HRID 1404369ノート

反応式

HRID 1404369 の反応式
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[I:11][C:12]1[C:13]([O:21][CH3:22])=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16]>C1COCC1>[I:11][C:12]1[C:13]([O:21][CH3:22])=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16]

参加物

5

反応物 3

HCID 6386tert-ButanolHCID 867229723-Iodo-2-methoxy-benzoyl chlorideHCID 178418339Butyllithium

生成物 1

HCID 86722973Tert-butyl 3-iodo-2-methoxybenzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cooled (−5° C.) solution of tert-butanol (12.87 mL, 30 mmol) in THF (30 mL) was added, dropwise, BuLi (12.0 mL, 2.5 M in hexanes, 30 mmol). On complete addition, the solution was stirred for 20 minutes. To this solution is added a solution of 3-Iodo-2-methoxy-benzoyl Chloride (8.8 g, 29.8 mmol) in THF (12 mL). On complete addition, the cold bath was removed and stirring continued for 1.5 hours. This solution was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by silica chromatography (50 g silica; eluted with 0-20% ethyl acetate in hexanes) to give the title compound as an oil.

後処理

  1. additionwas added
  2. additionOn complete addition
  3. additionOn complete addition
  4. customthe cold bath was removed
  5. stirringstirring
  6. waitcontinued for 1.5 hours
  7. additionThis solution was diluted with ethyl acetate
  8. washwashed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica chromatography (50 g silica; eluted with 0-20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8c0aa269b45c4b629d020eeaabc616b5
出典データセット
uspto-grants-2014_12
特許番号
US08912169B2

反応ノート

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