Hydrochloric Acid → 2-(2,6-Diethyl-4-methylphenyl)-5-([1,3]dioxolan-2-ylmethyl)cyclohexane-1,3-dione

HRID 1027369

반응식

HRID 1027369 반응식
[IH2+].[CH2:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=1B(O)O)[CH3:3].[OH2:16].[OH-:17].[Li+].Cl.C[O:21][CH2:22][CH2:23][O:24][CH3:25]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=1[CH:7]1[C:8](=[O:16])[CH2:9][CH:4]([CH2:2][CH:25]2[O:21][CH2:22][CH2:23][O:24]2)[CH2:5][C:6]1=[O:17])[CH3:3]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 168937Lithium hydroxide, monohydrateHCID 3715291Iodine, ion (I1+)HCID 57437319(2,6-Diethyl-4-methylphenyl)boronic acid

생성물 1

HCID 667251072-(2,6-Diethyl-4-methylphenyl)-5-([1,3]dioxolan-2-ylmethyl)cyclohexane-1,3-dione

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

The iodonium ylide (477 mg, 1.19 mmol) prepared in Step 3a is added to a mixture of 2,6-diethyl-4-methylphenylboronic acid (343 mg, 1.79 mmol), tetrabutylammonium bromide (385 mg, 1.19 mmol), lithium hydroxide monohydrate (151 mg, 3.57 mmol) and palladium (II) acetate (13 mgs) in a mixture of 1,2-dimethoxyethane (10.8 ml) and water (2.7 ml) and the reaction mixture is heated at 55° C. for 5 hours. The reaction is then cooled, dilute aqueous hydrochloric acid is added, and the mixture is extracted with ethyl acetate. The organic extracts are combined, washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-5-([1,3]dioxolan-2-ylmethyl)cyclohexane-1,3-dione

후처리

  1. temperatureThe reaction is then cooled
  2. extractionthe mixture is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-092fb6cee83243338803759582fbd833
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735322B2

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