Trifluoroacetic acid → 2-Benzyl-1-benzothiophene

HRID 1873121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873121
FC(F)(F)C(O)=O.[S:8]1[C:12]([CH:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)O)=[CH:11][C:10]2[CH:21]=[CH:22][CH:23]=[CH:24][C:9]1=2.[BH4-].[Na+].[OH-].[Na+]>CCOCC>[CH2:13]([C:12]1[S:8][C:9]2[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=2[CH:11]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 3311304Benzo[b]thiophen-2-yl(phenyl)methanolHCID 4311764Sodium borohydride

Produkt 1

HCID 127581572-Benzyl-1-benzothiopheneAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (105 mL) was added dropwise over a 35 minute period to a stirred suspension of benzo[b]thiophene-2-yl-(phenyl)-methanol (17.6 g, 73.2 mmol), sodium borohydride (13.75 g, 364 mmol) and ether (1.3 L). After an additional 5 hours the reaction mixture was added to 10% aqueous sodium hydroxide (1.3 L) and stirred for 30 minutes. The layers were separated and the ether phase was washed with brine (500 mL) and dried (MgSO4). The ether phase was concentrated to provide the title compound as a white solid (15.2 g, 92%): NMR (CDCl3); δ 7.73 (d, J=6 Hz, 1H, thiopheneH), 7.65 (d, J=7 Hz, 1H, thiopheneH), 7.20-7.38 (m, 7H), 7.00 (s, 1H, thiopheneH), 4.22 (s, 2H, CH2).

Aufarbeitung

  1. customThe layers were separated
  2. washthe ether phase was washed with brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationThe ether phase was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3673db59e4134161af0004ec1b7791c6
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06110962

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