Potassium Carbonate → Ethyl acetate hexane

HRID 511946

반응식

HRID 511946 반응식
Br[C:2]1[CH:11]=[CH:10]C=C2[C:3]=1[CH:4]=[CH:5]C=[C:7]2[CH2:12][OH:13].C[O:15][C:16]1C=C(C(F)(F)F)C=C[C:17]=1B(O)O.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].O.O1CCOCC1>[CH3:17][CH2:16][O:15][C:12]([CH3:7])=[O:13].[CH3:10][CH2:11][CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 18963829HCID 18963829, 화합물HCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acid

생성물 1

HCID 21226206Ethyl acetate hexane수율 86%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

(5-Bromonaphthalen-1-yl)methanol (150 mg), 2-methoxy-4-trifluoromethylphenylboronic acid (167 mg, 1.2 eq.), Pd(OAc)2 (14 mg, 0.1 eq.), Xphos (60 mg, 0.2 eq.), and K2CO3 (262 mg, 3 eq.) were combined in a flask with 5 mL dioxane and 1.6 mL H2O and degassed. Reaction mixture was then refluxed at 100° C. for 2 hours. Solution was cooled to room temperature then diluted with EtOAc and washed with saturated NaHCO3. The organic layer was dried over sodium sulfate and concentrated. Chromatography achieved using ISCO max gradient 35% EtOAc/hexane yielding product as a clear oil (55 mg, 86% yield). 1H NMR (400 MHz) (CDCl3) δ 8.24-8.22 (m, 1H), 7.64 (dd, J=8 Hz, J=8 Hz, 1H), 7.55 (d, J=8 Hz, 1H), 7.51 (d, J=8 Hz, 1H), 7.45-7.37 (m, 4H), 7.29 (s, 1H), 5.22 (s, 2H), 3.76 (s, 3H). 13C NMR (100 MHz) (CDCl3) δ157.45, 136.48, 136.27, 133.49, 132.21, 132.16, 131.47, 131.29, 131.15, 127.29, 126.61, 125.77, 125.48, 125.41, 123.88, 122.79, 117.44, 117.40, 107.72, 63.94, 55.76.

후처리

  1. customdegassed
  2. customReaction mixture
  3. temperatureSolution was cooled to room temperature
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bcb59a40a1fc42e68225740f882fa5a6
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102617B2

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