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t-Butyl bromide → Ethyl 2-(tert-butoxy)-2-(2-phenyl-1-benzothiophen-3-yl)acetate

HRID 590959
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반응식

HRID 590959 반응식
[OH:1][CH:2]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23](Br)([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.[Ag-]=O>[C:23]([O:1][CH:2]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:26])([CH3:25])[CH3:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 10485t-Butyl bromideHCID 70813709Ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate

생성물 1

HCID 70813740Ethyl 2-(tert-butoxy)-2-(2-phenyl-1-benzothiophen-3-yl)acetate수율 13.3%

시약·촉매·용매 2

HCID 178418778HCID 178418778, 화합물촉매HCID 8078Cyclohexane용매

실험 절차

A mixture of ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate (2c) (190 mg, 0.6 mmol), silver (I) oxide (417 mg, 1.8 mmol) and tertbutylbromide (360 μL, 3.2 mmol) in cyclohexane (5 mL) was vigorously stirred for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (2d) as a white solid (30 mg, 0.08 mmol, 13%).

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 90/10)

출처 및 근거

ORD 기록
ord-0cf6773b6f454af7bc07e8bcf90b7279
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238026B2

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