Cesium carbonate → ethyl {(1S)-5-[3-(4-bromo-2-methoxyphenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate

HRID 603412노트

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HRID 603412 반응식
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C@H:11]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9]2.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([O:29][CH3:30])[CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[C@H:11]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:9]3)=[C:24]([O:29][CH3:30])[CH:23]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2622344-Bromo-2-methoxyphenolHCID 16110497ethyl[(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate

생성물 1

HCID 59300414ethyl {(1S)-5-[3-(4-bromo-2-methoxyphenoxy)propoxy]-2,3-dihydro-1H-inden-1-yl}acetate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of ethyl [(1S)-5-(3-bromopropoxy)-2,3-dihydro-1H-inden-1-yl]acetate (1.4 g, 4.10 mmol) (Example 45) in DMF (130 mL, containing 1 vol % water) was added 4-bromo-2-methoxyphenol (832.9 mg, 4.10 mmol) followed by Cs2CO3 (2.66 g, 8.18 mmol). The reaction mixture was heated for 12 h at 80° C. Upon cooling to rt, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel flash chromatography (gradient 1:4 to 1:1 (v/v) EtOAc/hexane) to give the product as a colorless oil. 1H NMR (400 MHz, acetone-d6) δ 7.11-7.07 (m, 2H), 7.03-7.01 (m, 1H), 6.94-6.92 (m, 1H), 6.82-6.81 (m, 1H), 6.75-6.72 (m, 1H), 4.20-4.11 (m, 6H), 3.84 (s, 3H), 3.48-3.44 (m, 1H), 2.89-2.69 (m, 3H), 2.42-2.30 (m, 2H), 2.07 (q, 2H), 1.75-1.70 (m, 1H), 1.25 (t, 3H).

후처리

  1. temperatureUpon cooling to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel flash chromatography (gradient 1:4 to 1:1 (v/v) EtOAc/hexane)

출처 및 근거

ORD 기록
ord-5310d2ec6e914e068e5bd773e2b2882a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906653B2

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