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

HRID 370989

반응식

HRID 370989 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-7555993b5cea442e88037d537b6542ad
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04528399

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