Potassium Carbonate → HCID 13465704、化合物

HRID 915688

反応式

HRID 915688 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 13465704HCID 13465704、化合物収率 107.4%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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+]

後処理

  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

出典と根拠

ORDレコード
ord-da8fbbdf7e3c4730990c848a5e04d2f8
出典データセット
uspto-grants-2007_09
特許番号
US07265246B2

関連ノート

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