Acetone → 6,7-Dichloro-5-hydroxy-alpha,alpha-dimethylbenzo[b]thiophene-2-methanol

HRID 485898

反応式

HRID 485898 の反応式
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[C:10]=1[Cl:11].C([Li])CCC.C(Cl)(Cl)(Cl)Cl.C(=O)=O.[CH3:26][C:27]([CH3:29])=[O:28]>O1CCCC1.C(O)(=O)C.O>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[C:8]([C:27]([CH3:29])([CH3:26])[OH:28])[S:7][C:6]=2[C:10]=1[Cl:11]

参加物

8

反応物 4

HCID 180AcetoneHCID 132899976,7-Dichloro-1-benzothiophene-5-olHCID 86602444Carbontetrachloride dry-iceHCID 178418339Butyllithium

生成物 1

HCID 132900426,7-Dichloro-5-hydroxy-alpha,alpha-dimethylbenzo[b]thiophene-2-methanol

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 6,7-dichloro-5-hydroxybenzo[b]thiophene in 28 ml of dried tetrahydrofuran at -28° is added 21 ml of 2.5M n-butyllithium, maintaining the temperature below -18°. Following the addition, the carbon tetrachloride-dry ice bath is replaced with an ice-water bath and the mixture is stirred at 0°-5° for about 4 hrs. A solution of 3.3 ml of acetone in 10 ml tetrahydrofuran is added dropwise. After stirring for one hr, the solution is poured onto 100 ml of water and acidified to pH=5-6 with glacial acetic acid. The acidic solution is extracted with ethyl acetate, washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give 3.84 g of 6,7-dichloro-5-hydroxy-α,α-dimethylbenzo[b]thiophene-2-methanol, mp 171°-173°.

後処理

  1. temperaturemaintaining the temperature below -18°
  2. additionthe addition
  3. stirringAfter stirring for one hr
  4. extractionThe acidic solution is extracted with ethyl acetate
  5. washwashed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed

出典と根拠

ORDレコード
ord-18cbe684029f47c9b99e0d5f95ef1a29
出典データセット
uspto-grants-1985_08
特許番号
US04537976

関連ノート

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