Potassium Carbonate → HCID 13465704, 화합물

HRID 915688

반응식

HRID 915688 반응식
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=[O:8].[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:9]1([C:2]2[CH:6]=[CH:5][O:4][C:3]=2[CH:7]=[O:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 33672713-Bromo-2-furaldehyde

생성물 1

HCID 13465704HCID 13465704, 화합물수율 107.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

Prepare a mixture of 3-bromofuran-2-carbaldehyde (381 mg, 2.19 mmol), phenylboronic acid (534 mg, 4.38 mmol), and 2M potassium carbonate (3.28 mL, 6.57 mmol) in 1,2-dimethoxyethane (20 mL). Bubble nitrogen into this mixture for 20 minutes. Add Pd2(dba)3 (68 mg, 0.06 mmol) and PPh3 (68 mg, 0.26 mmol) and purge the mixture with nitrogen for an additional 10 minutes. Then heat the mixture to 80° C. After 24 hours, evaporate the solvent and redissolve the residue in ethyl acetate. Extract the aqueous phase with ethyl acetate (2×10 mL), wash the combined organic phases with brine (40 mL), dry (magnesium sulfate), filter and concentrate. Perform flash chromatography on silica gel eluting with 5:1 hex/ethyl acetate to afford 405 mg of the title compound as a white solid. MS: m/e=173 [MH+]

후처리

  1. customPrepare
  2. waitAfter 24 hours
  3. customevaporate the solvent
  4. dissolutionredissolve the residue in ethyl acetate
  5. extractionExtract the aqueous phase with ethyl acetate (2×10 mL)
  6. washwash the combined organic phases with brine (40 mL)
  7. dry with materialdry (magnesium sulfate)
  8. filtrationfilter
  9. concentrationconcentrate

출처 및 근거

ORD 기록
ord-da8fbbdf7e3c4730990c848a5e04d2f8
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265246B2

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