Boron tribromide → 1-Benzyl-2-ethyl-1H-indol-4-OL

HRID 49454

反応式

HRID 49454 の反応式
[CH2:1]([C:3]1[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([O:12]C)[CH:8]=[CH:7][CH:6]=2)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 99432411-Benzyl-2-ethyl-4-methoxy-1H-indole

生成物 1

HCID 98164161-Benzyl-2-ethyl-1H-indol-4-OL収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3.1 g (11.7 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole was O-demethylated by treating it with 48.6 mL of 1M BBr3 in methylene chloride with stirring at room temperature for 5 hours, followed by concentration at reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.58 g (54% yield) of 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole, mp, 86-90° C.

後処理

  1. concentrationfollowed by concentration at reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

出典と根拠

ORDレコード
ord-a043990a7bc440729a55c750861f88eb
出典データセット
uspto-grants-2004_03
特許番号
US06706752B1

関連ノート

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