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

HRID 47951ノート

反応式

HRID 47951 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a0cfbe59340489193659de144a8f45d
出典データセット
uspto-grants-2004_03
特許番号
US06700001B2

反応ノート

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