1,2-Dimethoxyethane → HCID 21071796, 화합물

HRID 1372166노트

반응식

HRID 1372166 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:19]1[C:27]2[O:26][CH:25]=[CH:24][C:23]=2[CH:22]=[C:21]([CH3:28])[CH:20]=1.COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:19]2[C:27]3[O:26][CH:25]=[CH:24][C:23]=3[CH:22]=[C:21]([CH3:28])[CH:20]=2)=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 210718017-Bromo-5-methyl-1-benzofuran

생성물 1

HCID 21071796HCID 21071796, 화합물수율 91%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 4-methoxyphenylboronic acid (4.76 g, 31.3 mmol), Na2CO3 (32.6 2 N aqueous, 65.2 mmol), Pd(PPh3)4 (1.5 g, 1.3 mmol), 7-bromo-5-methylbenzofuran (5.5 g, 26.1 mmol), and ethylene glycol dimethyl ether (275 ml) was heated to reflux for 12 h. The reaction was cooled, ether (500 ml) was added and the layers separated. The aqueous was further extracted with ether and the organic layers were dried over anhydrous Na2SO4, passed through a silica plug and concentrated to 7.16 g brown oil. Further purification by column chromatography (10% EtOAc/hexanes) afforded 5.62 g (91%) product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 3.44 (3H, s), 3.82 (3H, s), 6.94 (1H, d, J=2.2 Hz), 7.108 (2H, d, J=8.8 Hz), 7.30 (1H, s), 7.38 (1H, s), 7.81 (2H, d, J=8.8 Hz), 8.00 (1H, d, J=2.2 Hz).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. temperatureThe reaction was cooled
  4. customthe layers separated
  5. extractionThe aqueous was further extracted with ether
  6. dry with materialthe organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated to 7.16 g brown oil
  8. customFurther purification by column chromatography (10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-cc029056401141c68e021c347462c23b
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157491B2

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