Sodium borohydride → [3-(Cyclopropylmethoxy)phenyl]methanol

HRID 1006244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006244
[BH4-].[Na+].[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[CH2:5][CH2:4]1>CO>[OH:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)[CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 220482703-(Cyclopropylmethoxy)benzaldehyde

Produkt 1

HCID 22676783[3-(Cyclopropylmethoxy)phenyl]methanolAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (0.75 g, 20 mmol) was added in portions to a stirred solution of 3-(cyclopropylmethoxy)benzaldehyde (Lit: Chem. Pharm. Bull. 1975, 23, 2878) (3.5 g, 20 mmol) in methanol (80 mL). The mixture was stirred for 2 h and then quenched with water (300 mL). The product was extracted with ethyl acetate (3×150 mL) and then the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to leave 3.2 g (89%) of crude product. This material was used in the next reaction without further purification or analysis.

Aufarbeitung

  1. customquenched with water (300 mL)
  2. extractionThe product was extracted with ethyl acetate (3×150 mL)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-033b87ce59c14cb692d82a2d022a6a29
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787651B2

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