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

HRID 49454

반응식

HRID 49454 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a043990a7bc440729a55c750861f88eb
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706752B1

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