Triphenylphosphine → 3-(3-Cyclopentyloxy-4-methoxyphenyl)-3-(3-nitrophenylethynyl)cyclohexan-1-one

HRID 442708노트

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HRID 442708 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:25]1[CH:26]=[C:27]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:29][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=4)[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 125741-Iodo-3-nitrobenzeneHCID 153920073-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one

생성물 1

HCID 158590573-(3-Cyclopentyloxy-4-methoxyphenyl)-3-(3-nitrophenylethynyl)cyclohexan-1-one수율 90.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

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온도
80 °C

실험 절차

To a solution of the compound from Example 3 (E1) (0.2 g, 0.64 mmol) and 3-iodonitrobenzene (Aldrich, 0.16 g, 0.64 mmol) in triethylamine (4 mL) under an argon atmosphere was added trace tetrakis(triphenylphosphine)palladium(0), copper(I) iodide and triphenylphosphine. The mixture was heated at 80° C. for 0.2 h, was cooled to room temperature and was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, was dried (MgSO4) and was evaporated. Purification by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, provided the title compound as yellow solid (0.25 g, 90%), m.p. 46°-48° C.

후처리

  1. temperaturewas cooled to room temperature
  2. concentrationwas concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialwas dried (MgSO4)
  6. customwas evaporated
  7. customPurification by flash chromatography
  8. washeluting with 3:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-98d4b94520ba4344b4e2e4dbea491123
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891883

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