Sodium Carbonate → HCID 22634660、化合物

HRID 1057956ノート

反応式

HRID 1057956 の反応式
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=1.[C:12]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[C:12]([C:16]1[CH:17]=[C:18]([C:2]2[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:6]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23])([CH3:15])([CH3:13])[CH3:14]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 106321513-Tert-butyl-4-methoxyphenylboronic acidHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

生成物 1

HCID 22634660HCID 22634660、化合物収率 101.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

260 mg (0.5 mmol) of tetrakis(triphenylphosphine)palladium(0), 50 ml of toluene and 2.59 g (10.9 mmol) of ethyl 2-bromo-4-thiophenecarboxylate are introduced into a three-necked flask under a stream of nitrogen and the mixture is stirred at room temperature for 20 minutes. 3.7 g (16.5 mmol) of 3-tert-butyl-4-methoxyphenylboronic acid and 11 ml of aqueous sodium carbonate solution (2 N) are then added and the mixture is refluxed for 8 hours. The reaction medium is evaporated to dryness, the residue is taken up in water and ethyl ether and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and heptane (10/90% by volume). 3.53 g (69%) of ethyl 2-(3-tert-butyl-4-methoxyphenyl)-4-thiophenecarboxylate are obtained.

後処理

  1. temperaturethe mixture is refluxed for 8 hours
  2. customThe reaction medium is evaporated to dryness
  3. customethyl ether and the organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluted with a mixture of ethyl acetate and heptane (10/90% by volume)

出典と根拠

ORDレコード
ord-ffc3ff25127349f3a6e248030877d86f
出典データセット
uspto-grants-2003_02
特許番号
US06515021B1

反応ノート

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