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t-Butyl bromide → ethyl 2-(tert-butoxy)-2-(1-phenyl-1H-indol-2-yl)acetate

HRID 590968
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HRID 590968 반응식
[OH:1][CH:2]([C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23](Br)([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.ClCCl.[Ag-]=O>[C:23]([O:1][CH:2]([C:8]1[N:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:26])([CH3:25])[CH3:24]
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참가 물질

6

반응물 2

HCID 10485t-Butyl bromideHCID 70813712ethyl 2-hydroxy-2-(1-phenyl-1H-indol-2-yl)acetate

생성물 1

HCID 70813717ethyl 2-(tert-butoxy)-2-(1-phenyl-1H-indol-2-yl)acetate수율 33.5%

시약·촉매·용매 3

HCID 178418778HCID 178418778, 화합물촉매HCID 6344Dichloromethane용매
HCID 8078
Cyclohexane
용매

실험 절차

A mixture of ethyl 2-hydroxy-2-(1-phenyl-1H-indol-2-yl)acetate (5b) (50 mg, 0.17 mmol), silver (I) oxide (130 mg, 0.56 mmol) and tertbutylbromide (114 μL, 1.02 mmol) in cyclohexane (4 mL) and dichloromethane (2 mL) was vigorously stirred for 24 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5) to afford the desired ether oxide (5c) as a white solid (20 mg, 0.057 mmol, 33%).

후처리

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5)

출처 및 근거

ORD 기록
ord-0417813cc9364e73b8888f67d7baddea
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238026B2

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