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Diethyl Ether → 2(5H)-Furanone, 4-[4-(methylthio)phenyl]-3-phenyl-

HRID 1107884
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HRID 1107884 반응식
I[C:2]1[C:3](=[O:15])[O:4][CH2:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>C1C=CC=CC=1.[OH-].[Na+]>[C:16]1([C:2]2[C:3](=[O:15])[O:4][CH2:5][C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 11773TriphenylarsineHCID 66827Phenylboronic AcidHCID 121505903-iodo-4-(4-(methylthio)phenyl)-2-(5H)-furanone

생성물 1

HCID 110442352(5H)-Furanone, 4-[4-(methylthio)phenyl]-3-phenyl-

시약·촉매·용매 2

HCID 241Benzene용매
HCID 14798
Sodium Hydroxide
용매

실험 절차

A mixture of 4 g of the product of Step 3, 3.7 g of PhB(OH)2, 0.4 g of Ph3As, 0.4 g of PdCl2 (PhCN)2 in 100 mL of benzene and 15 mL of 2N NaOH is refluxed for 6 h. After cooling to r.t., Et2O (200 mL) is added to the reaction mixture and the mixture is washed with 100 mL of saturated NaHCO3. The organic layer is dried over MgSO4 and concentrated. The residue is purified by flash chromatography on silica gel eluted with 4:1 hexane/EtOAc to give the title compound.

후처리

  1. temperatureis refluxed for 6 h
  2. washthe mixture is washed with 100 mL of saturated NaHCO3
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography on silica gel
  6. washeluted with 4:1 hexane/EtOAc

출처 및 근거

ORD 기록
ord-e443f5026e834a07b7d922226dffc299
출처 데이터셋
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06063811

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