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2-Ethylthiophene → HCID 86754562, 화합물

HRID 619626
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HRID 619626 반응식
[CH2:1]([C:3]1[S:4][CH:5]=[CH:6][CH:7]=1)[CH3:2].C([Li])CCC.[CH3:13][C:14]1([CH3:45])[CH:23]=[C:22](OS(C(F)(F)F)(=O)=O)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:32]#[C:33][C:34]3[CH:44]=[CH:43][C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][CH:35]=3)[CH:20]=2)[S:15]1>C1COCC1.[Cl-].[Cl-].[Zn+2].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([C:3]1([C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:32]#[C:33][C:34]4[CH:44]=[CH:43][C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:36][CH:35]=4)[CH:20]=3)[S:15][C:14]([CH3:13])([CH3:45])[CH:23]=2)[CH2:7][CH:6]=[CH:5][S:4]1)[CH3:2]
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HCID 133882-EthylthiopheneHCID 10051511ethyl 4-(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-thio-chromen-6-ylethynyl)-benzoate2회HCID 178418339Butyllithium

생성물 1

HCID 86754562HCID 86754562, 화합물

시약·촉매·용매 3

HCID 3007855Zincchloride촉매
HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

A solution of 2-ethylthiophene (112.0 mg, 1.00 mmol) in 2.0 mL of THF was cooled to -78° C. and n-butyllithium (64.0 mg, 1.00 mmol, 0.63 ml of a 1.6M solution in hexanes) was added and the solution warmed to 0° C. during 1.5 hours. A solution of ZnCl2 (218.0 mg, 1.60 mmol) in 3.0 mL THF was slowly added via cannula. The resulting solution was warmed to room temperature, stirred for 40 minutes, and transferred via cannula to a solution of ethyl 4-[(2,2-dimethyl-4-trifluoromethanesulfonyloxy-(2H)-thiochromen-6-yl)ethynyl]-benzoate (Compound 224, 200.0 mg, 0.40 mmol) and tetrakis(triphenylphosphine) palladium(0) (24.0 mg, 0.02 mmol) in 2.0 mL THF. This solution was heated to 50° C. for 2 hours, cooled to room temperature, and the reaction quenched by the addition of saturated aqueous NH4Cl. The solution was extracted with EtOAc and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 29.0 mg (16%), was isolated by HPLC (1.25% EtOAc/hexanes) as a pale-yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.01 (2H, d, J=8.4 Hz), 7.65 (1H, s), 7.55 (2H, d, J=8.4 Hz), 7.35 (2H, s), 6.84 (1H, d, J=3.5 Hz), 6.77 (1H, m), 6.02 (1H, s), 4.39 (2H, q, J=7.1 Hz), 2.88 (2H, q, J=7.6 Hz), 1.46 (6H, s), 1.41 (2H, t, J=7.1 Hz), 1.35 (2H, t, J=7.6 Hz),

후처리

  1. temperatureThe resulting solution was warmed to room temperature
  2. temperatureThis solution was heated to 50° C. for 2 hours
  3. temperaturecooled to room temperature
  4. customthe reaction quenched by the addition of saturated aqueous NH4Cl
  5. extractionThe solution was extracted with EtOAc
  6. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  7. dry with materialbefore being dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a708faf232f145f8bae8e831f9a04b84
출처 데이터셋
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05958954

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