Hydrochloric Acid → Ethyl 7-(4-fluorobenzoyl)-8-oxononanoate

HRID 860413노트

반응식

HRID 860413 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([C:10](=[O:12])[CH3:11])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:13])=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 4326551-(4-Fluoro-phenyl)-butane-1,3-dione

생성물 1

HCID 57444527Ethyl 7-(4-fluorobenzoyl)-8-oxononanoate

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of 1-(4-fluorophenyl)butane-1,3-dione (1.0 g), potassium carbonate (3.84 g), and tetrabutylammonium bromide (90 mg) in toluene (20 ml) was refluxed for 3 hours, then ethyl 6-bromohexanoate (1.18 ml) was added. After stirring at 100° C. for 3 hours, the mixture was partitoned between ethyl acetate and 0.5N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give ethyl 7-(4-fluorobenzoyl)-8-oxononanoate (983 mg) as an oil.

후처리

  1. temperaturewas refluxed for 3 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)

출처 및 근거

ORD 기록
ord-1b492a1ead7a4f64b5ca605ce0ca112b
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153854B2

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