Borane → (3-Chloro-1-benzothien-2-yl)methanol

HRID 604624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604624
B.[Cl:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]=1[C:12](O)=[O:13]>C1COCC1>[Cl:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]=1[CH2:12][OH:13]

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 3079643-Chloro-1-benzothiophene-2-carboxylic acid

Produkt 1

HCID 821965(3-Chloro-1-benzothien-2-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Borane (1M in THF, 6.11 mL, 6.11 mmol) was added to a stirred suspension of 3-chloro-1-benzothiophene-2-carboxylic acid (1.00 g, 4.70 mmol) in dry THF (2 mL) at 0° C. under N2. The reaction was allowed to warm to room temperature and was heated at reflux for 1½ h. The reaction was quenched with water (5 mL) and saturated K2CO3 (10 mL), then extracted with EtOAc (3×30 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-chloro-1-benzothien-2-yl)methanol. 1H NMR (500 MHz, CDCl3): δ 7.79-7.77 (m, 2H); 7.45-7.42 (m, 1H); 7.39-7.36 (m, 1H); 4.96 (s, 2H); 2.48 (s, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 1½ h
  3. customThe reaction was quenched with water (5 mL) and saturated K2CO3 (10 mL)
  4. extractionextracted with EtOAc (3×30 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-87448e66ea6343c0bc97ea47ca06154c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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