Sodium Carbonate → 6-[(1E)-3-Methoxyprop-1-en-1-yl]indan-1-one

HRID 337646노트

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HRID 337646 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB(/[CH:20]=[CH:21]/[CH2:22][O:23][CH3:24])O1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[CH3:24][O:23][CH2:22]/[CH:21]=[CH:20]/[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 1397781-Indanone, 6-bromo-HCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 670621216-[(1E)-3-Methoxyprop-1-en-1-yl]indan-1-one

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 6-bromoindan-1-one (1 eq.) and 4,4,5,5-tetramethyl-2-[(1E)-3-(methyloxy)-1-propen-1-yl]-1,3,2-dioxaborolane (1.3 eq.) in DMF (0.1 M) was added trans-bis(triphenylphosphine) palladium(II) bromide (0.05 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, 2 M aq. Na2CO3 (3 eq.) was added and the resulting mixture was stirred at 100° C. for 1 h. The now black suspension was cooled to RT, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a beige solid.

후처리

  1. customThe vessel was repeatedly evacuated
  2. additionback-filled with nitrogen
  3. temperatureThe now black suspension was cooled to RT
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-b7b3220edbcd45aeae64b537e9a9fbc3
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

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