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

HRID 576935

Reaktionsgleichung

Reaktionsgleichung von HRID 576935
[BH4-].[Na+].[Cl:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]=1[CH:13]=[O:14].O>C(O)C>[Cl:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]=1[CH2:13][OH:14]

Komponenten

5

Edukt 3

HCID 962WaterHCID 8181213-Chloro-1-benzothiophene-2-carbaldehydeHCID 4311764Sodium borohydride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of sodium borohydride (231 mg, 6.1 mmol) in absolute ethanol (10 mL) was added a solution of 3-chloro-1-benzothiophen-2-carbaldehyde (1.0 g, 5.1 mmol) in absolute ethanol (5 mL) at 0° C. The mixture was stirred for 2 hours at room temperature. Water was added and extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (3-chloro-1-benzothiophen-2-yl)methanol was obtained as an orange pale solid (944 mg, 94% yield) and used for next step without further purification; 1H NMR (400 MHz, CDCl3): δ 2.17 (bs, 1H), 4.99 (s, 2H), 7.37-7.47 (m, 2H), 7.78-7.82 (m, 2H).

Aufarbeitung

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-f5d2a07b6f6b4d1bb19fc8e2326074f5
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

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