Sodium borohydride → [1-(Benzyloxy)-2-naphthyl]methanol

HRID 47951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47951
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH:19]=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 156178221-(Benzyloxy)-2-naphthaldehyde

Produkt 1

HCID 23431826[1-(Benzyloxy)-2-naphthyl]methanolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(benzyloxy)-2-naphthaldehyde (7.00 g, 26.7 mmol) in methanol (250 mL) at 0° C. is added sodium borohydride (1.51 g, 40.0 mmol) and the reaction mixture is allowed to stir at room temperature for 24 h. The solvent is removed in vacuo to give a crude solid which is partitioned between ethyl acetate (300 mL) and water (300 mL). The organic layer is separated and washed with water (300 mL), aqueous sodium chloride (300 mL), dried (magnesium sulfate) and filtered through a plug of silica (10 cm×5 cm). The solvent is removed in vacuo to give 6.98 g (99%) of [1-(benzyloxy)-2-naphthyl]methanol as white crystalline solid. Rf=0.36 (silica, dichloromethane:hexanes 3:2); mp 85-87° C. Anal. Calcd. for C18H16O2: C, 81.24; H, 6.14. Found: C, 81.03; H, 5.98.

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customto give a crude solid which
  3. customis partitioned between ethyl acetate (300 mL) and water (300 mL)
  4. customThe organic layer is separated
  5. washwashed with water (300 mL), aqueous sodium chloride (300 mL)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered through a plug of silica (10 cm×5 cm)
  8. customThe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a0cfbe59340489193659de144a8f45d
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06700001B2

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