Metaperiodic acid → 4-[4-(Difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid

HRID 1643766노트

반응식

HRID 1643766 반응식
I(O)(=O)(=O)=[O:2].[F:6][CH:7]([F:31])[C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH:22]=[O:23])[O:21][C:17]=3[CH:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=2)=[CH:10][CH:9]=1>CC#N.C(OCC)(=O)C.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](F)([O-])(=O)=O>[F:31][CH:7]([F:6])[C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([C:22]([OH:2])=[O:23])[O:21][C:17]=3[CH:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=2)=[CH:10][CH:9]=1

참가 물질

6

반응물 2

HCID 65185Metaperiodic acidHCID 59559912Ethyl 4-[4-(difluoromethyl)phenoxy]-2-formyl-1-benzofuran-6-carboxylate

생성물 1

HCID 595601994-[4-(Difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid수율 96%

시약·촉매·용매 3

HCID 178479089HCID 178479089, 화합물촉매HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

To acetonitrile (10 mL) was added periodic acid (209 mg, 0.916 mmol) and stirred vigorously at room temperature for 15 min. Ethyl 4-[4-(difluoromethyl)phenoxy]-2-formyl-1-benzofuran-6-carboxylate (300 mg, 0.833 mmol) was then added (in ice-bath) followed by addition of pyridium fluorochromate (3.32.mg, 0.02 mmol) in CH3CN (5 mL). The reaction was stirred at 0° C. for 1 hour. The reaction was diluted with ethyl acetate and washed with brine/water (1:1), dried over MgSO4 and concentrated to give the title compound (300 mg, 96%) as an orange solid, which was usedin the next step without further purification. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.33 (t, J=7.16 Hz, 3 H) 4.33 (q, J=7.16 Hz, 2 H) 6.61 (t, J=56.52 Hz, 1 H) 7.06 (d, J=8.48 Hz, 2 H) 7.37 (s, 1 H) 7.43-7.54 (m, 3 H) 8.02 (s, 1 H).

후처리

  1. stirringThe reaction was stirred at 0° C. for 1 hour
  2. washwashed with brine/water (1:1)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c4561d1bd07640e9900ba2fce870a933
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119624B2

반응 노트

불러오는 중…