2,5-Dihydroxybenzoic acid → (2S)-2-methylbutyl 2,5-dihydroxybenzoate

HRID 424307

反応式

HRID 424307 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CS(O[CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])=[O:5]

参加物

5

反応物 3

HCID 34692,5-Dihydroxybenzoic acidHCID 516892Sodium BicarbonateHCID 15698189(2S)-2-Methylbutyl methanesulfonate

生成物 1

HCID 59005024(2S)-2-methylbutyl 2,5-dihydroxybenzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 2,5-dihydroxybenzoic acid (15.4 g) in DMF (50 ml) DBU (15.3 ml) was drop wise added. After complete addition (10 min) stirring was continued for 30 min at room temperature, then a solution of (2S)-2-methylbutyl methanesulfonate (16.4 g) in DMF (20 ml) was added drop wise. After complete addition (30 min) the reaction mixture was heated to 80° C. for 6 h. It was then cooled to room temperature, poured into saturated solution of NaHCO3 (200 ml) and extracted with ethyl acetate (2×300 ml). The combined extracts were dried over Na2SO4 and evaporated to dryness. The obtained dark oily residue was purified over silica gel column to give nearly pure (2S)-2-methylbutyl 2,5-dihydroxybenzoate as beige oil.

後処理

  1. additionwise added
  2. additionAfter complete addition (10 min)
  3. additionAfter complete addition (30 min) the reaction mixture
  4. temperatureIt was then cooled to room temperature
  5. extractionextracted with ethyl acetate (2×300 ml)
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. customevaporated to dryness
  8. customThe obtained dark oily residue was purified over silica gel column

出典と根拠

ORDレコード
ord-501a2af4992b46148731bbbee28ad177
出典データセット
uspto-grants-2012_01
特許番号
US08105662B2

関連ノート

読み込み中…