2-Methyl-3-butyn-2-ol → 2-Methyl-4-(5-methyl-3-phenyl-isoxazol-4-yl)-but-3-yn-2-ol

HRID 1984647

반응식

HRID 1984647 반응식
I[C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][O:5][C:6]=1[CH3:7].C(N(CC)CC)C.[CH3:21][C:22]([OH:26])([C:24]#[CH:25])[CH3:23]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][C:22]([OH:26])([C:24]#[C:25][C:2]1[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:4][O:5][C:6]=1[CH3:7])[CH3:23]

참가 물질

7

반응물 3

HCID 82582-Methyl-3-butyn-2-ol2회HCID 8471Triethylamine2회HCID 27761504-Iodo-5-methyl-3-phenylisoxazole

생성물 1

HCID 688532502-Methyl-4-(5-methyl-3-phenyl-isoxazol-4-yl)-but-3-yn-2-ol수율 78%

시약·촉매·용매 3

HCID 812191,3-Bis(diphenylphosphino)propane촉매2회HCID 167845palladium(II) acetate촉매2회HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 4-iodo-5-methyl-3-phenylisoxazole (5.73 g, 20.1 mmol), palladium(II) acetate (135 mg, 0.60 mmol), 1,3-bis(diphenylphosphino)propane (249 mg, 0.60 mmol), triethylamine (7.0 mL, 50.2 mmol) and 2-methyl-3-butyn-2-ol (3.0 mL, 30.7 mmol) in N,N-dimethylformamide (40 mL) was evaporated and flushed with argon. Cuprous iodide (77 mg, 0.40 mmol) was added and the reaction mixture was stirred for 23 h at 90° C. (after 1.75 h and 4.5 h, respectively, further palladium(II) acetate (135 mg, 0.60 mmol), 1,3-bis(diphenylphosphino)propane (249 mg, 0.60 mmol), triethylamine (7.0 mL, 50.2 mmol), 2-methyl-3-butyn-2-ol (3.0 mL, 30.7 mmol) and cuprous iodide (77 mg, 0.40 mmol) were added) before cooled to ambient temperature and separated between aqueous sodium hydroxide (1 M, 600 mL) and ethyl acetate (1000 mL). The aqueous layer was extracted with ethyl acetate (1000 mL) and washed with aqueous sodium hydroxide (1 M, 600 mL). The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=67:33) afforded the title compound (3.77 g, 78%) as a yellow oil. MS: m/e=242.2 [M+H]+.

후처리

  1. customwas evaporated
  2. customflushed with argon
  3. temperaturebefore cooled to ambient temperature
  4. customseparated between aqueous sodium hydroxide (1 M, 600 mL) and ethyl acetate (1000 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (1000 mL)
  6. washwashed with aqueous sodium hydroxide (1 M, 600 mL)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated
  9. customPurification by chromatography (SiO2, heptane:ethyl acetate=67:33)

출처 및 근거

ORD 기록
ord-eef96f50c0cd4a6a8e30c86abe2d91d4
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544704B2

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