Diethyl Ether → 5-Phenylthiophene-2-carbaldehyde

HRID 412004

反応式

HRID 412004 の反応式
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC>C1COCC1.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>[C:9]1([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 784285-Bromothiophene-2-carbaldehyde

生成物 1

HCID 1770535-Phenylthiophene-2-carbaldehyde収率 91.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

5-Bromothiophene-2-carboxaldehyde (1.0 g, 5.2 mmol) is added to a solution of tetrakis(triphenylphosphine)palladium(0) (180 mg, 0.16 mol) in degassed THF (10 mL). The resulting solution is stirred for 5 minutes and then a solution of phenylboronic acid (760 mg, 6.2 mmol) in THF (10 mL) is added followed by aqueous Na2CO3 (2M, 5.2 mL). The mixture is heated at reflux for 24 h. The reaction mixture is allowed to cool, poured into ether, and washed twice with water. The ether layer is dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (1:1 hexanes/CH2Cl2) to yield 900 mg (91%) of 5-phenylthiophene-2-carboxaldehyde. 1H NMR (300MHz, CDCl3)δ7.38-7.45, 7.65-7.68, 7.73, 9.88.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 h
  3. temperatureto cool
  4. washwashed twice with water
  5. dry with materialThe ether layer is dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (1:1 hexanes/CH2Cl2)

出典と根拠

ORDレコード
ord-9042e8cf7efe4b88ac999d58addddc10
出典データセット
uspto-grants-2003_05
特許番号
US06562816B2

関連ノート

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