Potassium Carbonate → 5-(4-Methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester

HRID 424792ノート

反応式

HRID 424792 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[C:5]([CH3:12])[CH:4]=1.[CH3:13][O:14][C:15]([C:17]1[S:18][C:19](Br)=[C:20]([CH3:22])[CH:21]=1)=[O:16].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][O:14][C:15]([C:17]1[S:18][C:19]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH3:12])=[C:20]([CH3:22])[CH:21]=1)=[O:16]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 2795489Methyl 5-bromo-4-methylthiophene-2-carboxylate

生成物 1

HCID 667042235-(4-Methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester収率 39.1%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 4-methoxy-2-methylphenylboronic acid (912 mg, 6 mmol), 5-bromo-4-methyl-thiophene-2-carboxylic acid methyl ester (1.1 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in toluene (30 mL) and water (5 mL) is bubbled N2 for 15 minutes followed by addition of tetrakis(triphenylphosphine) palladium (289 mg, 0.25 mmol). The reaction mixture is stirred at 80° C. under N2 overnight. The reaction mixture is filtered through a diatomaceous earth pad eluting with EtOAc. The combined filtrate is concentrated and the residue is purified by column chromatography on silica gel eluting with 0-15% EtOAc in hexanes to give 5-(4-methoxy-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic acid methyl ester (540 mg, 39%). 1H NMR (CDCl3): δ 7.63 (s, 1H), 7.15 (d, 1H, J=8.4 Hz), 6.82 (d, 1H, J=2.8 Hz), 6.78 (dd, 1H, J=2.8, J=8.4 Hz), 4.79 (bs, 1H), 3.88 (s, 3H), 3.83 (s, 3H), 2.17 (s, 3H), 2.02 (s, 3H).

後処理

  1. customis bubbled N2 for 15 minutes
  2. filtrationThe reaction mixture is filtered through a diatomaceous earth pad
  3. washeluting with EtOAc
  4. concentrationThe combined filtrate is concentrated
  5. customthe residue is purified by column chromatography on silica gel eluting with 0-15% EtOAc in hexanes

出典と根拠

ORDレコード
ord-2f2beeb32f9641ea98cfa1f7a9d1f493
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

反応ノート

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