Propanal → HCID 13290045, Verbindung

HRID 370991

Reaktionsgleichung

Reaktionsgleichung von HRID 370991
[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.[CH:18](=[O:21])[CH2:19][CH3:20]>O1CCCC1.CCCCCC>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[CH:9]=[C:8]([CH:18]([CH2:19][CH3:20])[OH:21])[S:7][C:6]=2[C:10]=1[Cl:11]

Komponenten

6

Edukt 3

HCID 527PropanalHCID 132899976,7-Dichloro-1-benzothiophene-5-olHCID 178418339Butyllithium

Produkt 1

HCID 13290045HCID 13290045, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 7.0 g of 6,7-dichloro-5-hydroxybenzo[b]thiophene in 50 ml of dry tetrahydrofuran is cooled to -30°, using a dry ice-carbon tetrachloride bath and to the mixture is added dropwise, 35 ml of 2.2M n-butyllithium in hexane while the temperature is maintained below -20°. Following the addition, the bath is replaced with an ice-water bath and the reaction is stirred for 4 hrs at a temperature of 0°-5°. To the mixture is added dropwise solution of 3 ml of freshly distilled proprionaldehyde in 5 ml of tetrahydrofuran. The bath is removed. The reaction mixture is stirred for 20 mins and poured onto cold 10% hydrochloric acid. The mixture is extracted 3 times with ethyl ether. The combined ether extracts are washed, dried and the solvent is removed to give a solid. Recrystallization from ethyl ether and hexane gives 5.9 g of 6,7-dichloro-5-hydroxy-α-ethylbenzo[b]thiophene-2-methanol, mp 145°-145.5°.

Aufarbeitung

  1. additionto the mixture is added dropwise
  2. additionthe addition
  3. customthe bath is replaced with an ice-water bath
  4. customThe bath is removed
  5. stirringThe reaction mixture is stirred for 20 mins
  6. additionpoured onto cold 10% hydrochloric acid
  7. extractionThe mixture is extracted 3 times with ethyl ether
  8. washThe combined ether extracts are washed
  9. customdried
  10. customthe solvent is removed
  11. customto give a solid
  12. customRecrystallization from ethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-448866701b524b239f09b6bfd617f2dc
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528399

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