반응 #76229

반응 방정식

1-(benzyloxy)-2-naphthaldehyde

sodium borohydride

→

[1-(benzyloxy)-2-naphthyl]methanol

수율 99.0%

용매

methanol

반응 조건

후처리

1. 1
   기타The solvent is removed in vacuo
2. 2
   기타to give a crude solid which
3. 3
   기타is partitioned between ethyl acetate (300 mL) and water (300 mL)
4. 4
   기타The organic layer is separated
5. 5
   세척washed with water (300 mL), aqueous sodium chloride (300 mL)
6. 6
   건조dried (magnesium sulfate)
7. 7
   여과filtered through a plug of silica (10 cm×5 cm)
8. 8
   기타The solvent is removed in vacuo

실험 절차

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.

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