4-Iododibenzofuran → 4-Cyclohexyldibenzo[b,d]furan

HRID 929278노트

반응식

HRID 929278 반응식
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:10]1[C:15]2[O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:14]=2[CH:13]=[CH:12][CH:11]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Cl-].[Cl-].[Zn+2].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].C1COCC1>[CH:1]1([C:22]2[C:17]3[O:16][C:15]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:18]=3[CH:19]=[CH:20][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 3

HCID 4582574-IododibenzofuranHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 178478990HCID 178478990, 화합물

생성물 1

HCID 1178939144-Cyclohexyldibenzo[b,d]furan수율 90%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

ZnCl2 (13.6 g, 100.0 mmol) and THF (600 mL) were cooled to 0° C. After that, cyclohexylmagnesium chloride (70.0 mL, 70.0 mmol, 1M in THF) was added at 0° C. The mixture was stirred for 15 min from 0° C. to room temperature. The mixture was bubbled with nitrogen for 15 min, followed by the addition of 4-iododibenzo[b,d]furan (11.8 g, 40.0 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (3.3 g, 8.0 mmol), and Pd2(dba)3 (1.8 g, 2.0 mmol). The resultant mixture was bubbled with nitrogen for 15 min and stirred for 48 h. The reaction mixture was quenched by the addition of saturated K2CO3 solution and extracted with DCM. The extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography using 10% DCM/hexane to yield 4-cyclohexyldibenzo[b,d]furan (9.0 g, 90% yield) as a colorless oil.

후처리

  1. customThe mixture was bubbled with nitrogen for 15 min
  2. customThe resultant mixture was bubbled with nitrogen for 15 min
  3. stirringstirred for 48 h
  4. customThe reaction mixture was quenched by the addition of saturated K2CO3 solution
  5. extractionextracted with DCM
  6. dry with materialThe extracts were dried over MgSO4
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-9d3762a955ea4db1873138b3f8da8374
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09293712B2

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