Potassium Carbonate → Ethyl acetate hexane

HRID 511946

反応式

HRID 511946 の反応式
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]

参加物

9

反応物 4

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

生成物 1

HCID 21226206Ethyl acetate hexane収率 86%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-bcb59a40a1fc42e68225740f882fa5a6
出典データセット
uspto-grants-2015_08
特許番号
US09102617B2

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