Aluminium lithium hydride → [2-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-phenyl]-methanol

HRID 493096

Reaktionsgleichung

Reaktionsgleichung von HRID 493096
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][C:17]1[C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[S:20][C:21]=1[CH3:22]>C1COCC1>[CH3:22][C:21]1[S:20][C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[C:17]=1[S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][OH:8]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 688980832-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-benzoic acid methyl ester

Produkt 1

HCID 68898143[2-(2-Methyl-benzo[b]thiophen-3-ylsulfanyl)-phenyl]-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (250 mg, 6.6 mmol) is added to a solution of 2-(2-methyl-benzo[b]thiophen-3-ylsulfanyl)-benzoic acid methyl ester (651 mg, 2.07 mmol) in 10 mL dry THF at 0° C. The reaction mixture is stirred for 16 hours at room temperature. The reaction is quenched with 0.5 mL water. The reaction mixture is stirred for ½ hour and 0.25 mL 15% NaOH (aq) is added. The reaction mixture is stirred for 1 hour, then 1 mL water is added and stirring is continued for another hour. The mixture is filtered, dried with MgSO4 and concentrated in vacuo to give the title compound, which is used without further purification.

Aufarbeitung

  1. customThe reaction is quenched with 0.5 mL water
  2. stirringThe reaction mixture is stirred for ½ hour
  3. addition0.25 mL 15% NaOH (aq) is added
  4. stirringThe reaction mixture is stirred for 1 hour
  5. addition1 mL water is added
  6. stirringstirring
  7. waitis continued for another hour
  8. filtrationThe mixture is filtered
  9. dry with materialdried with MgSO4
  10. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f8d83c6e9aa34f75b5047f67cabcd8a6
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534791B2

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