Methanol → 3-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-ol

HRID 1749227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749227
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[Cl:15].[Li+].[BH4-].CO.[OH-].[Na+]>CCOCC>[Cl:15][C:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[S:10][C:6]=1[CH2:5][CH2:4][CH2:3][OH:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 667607513-(3-Chloro-benzo[b]thiophen-2-yl)-propionic acid methyl ester

Produkt 1

HCID 219644313-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-olAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

An ice cold solution of 3.63 g (14.3 mmol) of 15 in 60 mL of ether was treated with LiBH4 (621 mg, 28.5 mmol) and methanol (2 mL). After 30 min., 30 mL of 0.5 M NaOH solution was added. The mixture was extracted with ethyl acetate (2×25 mL) and the combined ethyl acetate solution washed with brine (50 mL), dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (5-20% ethyl acetate/hexane) to give 2.57 g (11.3 mmol, 79%) of the alcohol (16).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  2. washthe combined ethyl acetate solution washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (5-20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e2a22df8bc0f423392a971e7087ce02e
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156810B2

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