1,2-Dimethoxyethane → HCID 21071796、化合物

HRID 1372166ノート

反応式

HRID 1372166 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 21071796HCID 21071796、化合物収率 91%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cc029056401141c68e021c347462c23b
出典データセット
uspto-grants-2007_01
特許番号
US07157491B2

反応ノート

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