Hydrochloric Acid → 1,3-Benzodioxole-5-propanol

HRID 480357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 480357
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][C:18](O)=[O:19])=[CH:15][C:10]=2[O:9][CH2:8]1.Cl>C1COCC1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][CH2:17][CH2:18][OH:19])=[CH:15][C:10]=2[O:9][CH2:8]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 648103-(Benzodioxol-5-yl)propionic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 110304141,3-Benzodioxole-5-propanolAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (1M in THF, 30 mL, 30 mmol) was added slowly to a solution of 3-benzo[1,3]dioxol-5-yl-propionic acid (5.83 g, 30 mmol) in THF (60 mL) at 0° C. The reaction was warmed to room temperature and was stirred for 2 h. The solution was added in portions to a mixture of ice (200 g) and concentrated HCl (2 mL). The product was extracted into EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 6:4) provided the title alcohol (4.51 g). 1H NMR (400 MHz, CDCl3) δ 6.73-6.62 (m, 3H), 5.91 (s, 2H), 3.66 (t, 2H), 2.63 (t, 2H), 1.84 (m, 2H).

Aufarbeitung

  1. extractionThe product was extracted into EtOAc
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (hexanes:EtOAc 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-1195e017ce5a4ed789bd312bccc4eb92
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649657B2

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