Potassium Phosphate, Tribasic → 4-(Prop-1-en-2-yl)dibenzo[b,d]furan

HRID 717991

반응식

HRID 717991 반응식
I[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:23][C:24]1(C)[C:28](C)(C)OB(C(C)=C)O1>C1(C)C=CC=CC=1.O.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].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH2:23]=[C:24]([C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:28]

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 4582574-IododibenzofuranHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

생성물 1

HCID 177536004-(Prop-1-en-2-yl)dibenzo[b,d]furan수율 82%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매2회HCID 1140Toluene용매

실험 절차

4-Iododibenzo[b,d]furan (25 g, 85.0 mmol) and potassium phosphate (58.7 g, 255 mmol) were dissolved in 500 mL of toluene and 50 mL of water. The reaction was purged with nitrogen for 20 minutes and then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (15.98 mL, 85 mmol), Pd2(dba)3 (1.55 g, 1.7 mmol) and S-Phos (2.79 g, 6.8 mmol) were added. The reaction was refluxed for 18 hours. After cooling the reaction to room temperature, 100 mL of water was added, the organic and aqueous layers were separated, and the aqueous layer was extracted twice with 100 mL of ethyl acetate. The organic layers were passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 3% ethyl acetate in hexane to 5% ethyl acetate in hexane, v/v) to yield 14.5 g (82%) of pure product.

후처리

  1. customThe reaction was purged with nitrogen for 20 minutes
  2. temperatureThe reaction was refluxed for 18 hours
  3. temperatureAfter cooling
  4. customthe reaction to room temperature
  5. customthe organic and aqueous layers were separated
  6. extractionthe aqueous layer was extracted twice with 100 mL of ethyl acetate
  7. washeluting with DCM
  8. customAfter evaporation of the solvent

출처 및 근거

ORD 기록
ord-3813ada44f0e49d98ff94d8e963f66bb
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193745B2

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