Cyclohexane → o-Nitrophenyl cyclopropyl ketone

HRID 342191노트

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HRID 342191 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:15])[CH2:11][CH2:12][CH2:13]Br)([O-:3])=[O:2].C([N-]C(C)C)(C)C.[Li+].C1CCCCC1.[NH4+].[Cl-]>O1CCCC1>[CH:11]1([C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[O:15])[CH2:13][CH2:12]1

참가 물질

6

반응물 4

HCID 8078CyclohexaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 537739744-Bromo-2'-nitrobutyrophenone

생성물 1

HCID 10487947o-Nitrophenyl cyclopropyl ketone수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 1 (o-nitrophenyl)-4-bromo-1-butanone (0.75 g, 2.75 mmol) in dry tetrahydrofuran (THF) under nitrogen is cooled to -78° C. with stirring, cautiously treated with 2.21 ml of 1.5M lithium diisopropylamide (LDA) in cyclohexane (3.3 mmol LDA), held at -78° C. for 1 hour, allowed to warm to 0° C. for 2 hours and poured onto a saturated NH4Cl solution. The resultant mixture is extracted with ethyl acetate. The extracts are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give a residue. The residue is purified by flash column chromatography (silica gel; gradient 15%→25% ethyl acetate in hexane as eluent) to give the title product as a yellow oil, 0.34 g, 64% yield, identified by NMR and mass spectral analyses.

후처리

  1. extractionThe resultant mixture is extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue is purified by flash column chromatography (silica gel; gradient 15%→25% ethyl acetate in hexane as eluent)

출처 및 근거

ORD 기록
ord-c38942d0b3a0445ba883b0aaf0c69388
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856576

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