1,2-Dimethoxyethane → HCID 66679999, 화합물

HRID 537683

반응식

HRID 537683 반응식
[IH2+].[CH2:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:5]=1B(O)O)[CH3:3].[OH2:14].[OH-:15].[Li+].CO[CH2:19][CH2:20][O:21][CH3:22]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:2][CH3:3])=[C:5]([CH:7]2[C:8](=[O:14])[CH2:9][C:4]3([CH2:19][CH2:20][O:21][CH2:22][CH2:2]3)[CH2:5][C:6]2=[O:15])[CH:6]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 168937Lithium hydroxide, monohydrateHCID 3715291Iodine, ion (I1+)HCID 594459412-Ethyl-5-bromophenylboronic acid

생성물 1

HCID 66679999HCID 66679999, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A portion of the iodonium ylide (2.0 g, 5.21 mmol) is added to a mixture of 2-ethyl-5-bromophenylboronic acid (1.43 g, 6.25 mmol), palladium(II) acetate (59 mg, 0.26 mmol) and lithium hydroxide monohydrate (0.656 g, 15.6 mmol) in 1,2-dimethoxyethane (40 ml) and water (10 ml), and the mixture is heated at 50° C. for 6 hours, and then allowed to stand at room temperature overnight. The mixture is filtered through diatomaceous earth, washing the filter cake with water (50 ml) and ethyl acetate (50 ml). The organic phase is discarded. The aqueous phase is acidified to pH2 by addition of concentrated hydrochloric acid, and then extracted with ethyl acetate. The organic extract is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 9-(5-bromo-2-ethylphenyl)-3-oxaspiro[5.5]undecane-8,10-dione.

후처리

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. washwashing the filter cake with water (50 ml) and ethyl acetate (50 ml)
  3. additionThe aqueous phase is acidified to pH2 by addition of concentrated hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialis dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-145deb73b74741cb952ea9c9df55a26f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865623B2

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