5-(Benzyloxy)-2-hydroxybenzaldehyde → 4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol

HRID 398168ノート

反応式

HRID 398168 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:16]=1)[CH:14]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:17])=[C:13]([CH:14]([OH:15])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 8783625-(Benzyloxy)-2-hydroxybenzaldehydeHCID 178506676HCID 178506676、化合物

生成物 1

HCID 222611734-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenol収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of phenol (Kappe, T.; Witoszynskyj, T. Arch. Pharm. (1975), 308 (5), 339-346) (1.14 g, 5.00 mmol) in THF (15 mL) was cooled in a dry ice/acetone bath and treated dropwise with phenyllithium (7.5 mL, 13.5 mmol, 1.8M in cyclohexane/ethyl ether 70/30). The reaction mixture was allowed to warm gradually to ambient temperature. After 18 h, the reaction was quenched with aqueous saturated NH4Cl solution (1 mL) and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated to a brown oil (2.3 g). The crude product was purified by flash chromatography using hexanes:ethyl acetate (3:1 to 2:1) to give a pale yellow oil (1.42 g, 93%): 1H NMR (400 MHz, CDCl3) δ2.79 (s, 1H), 4.92 (s, 2H), 5.95, (s, 1H), 6.51 (s, 1H), 6.81 (d, 3H, J=1.5 Hz), 7.28-7.38 (s, 10H); MS (ES) m/e 305 [M−1].

後処理

  1. customthe reaction was quenched with aqueous saturated NH4Cl solution (1 mL)
  2. custompartitioned between ethyl acetate (50 mL) and 1N HCl (20 mL)
  3. washThe organic layer was washed with brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to a brown oil (2.3 g)
  6. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-ede1f8734837448495428e80c2d4686a
出典データセット
uspto-grants-2003_08
特許番号
US06610696B2

反応ノート

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