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

HRID 370989

Reaktionsgleichung

Reaktionsgleichung von HRID 370989
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7555993b5cea442e88037d537b6542ad
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528399

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