Ethyl Acetate → 5-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-4-methyl-thiophene-2-carboxylic Acid Methyl Ester

HRID 546838

反応式

HRID 546838 の反応式
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[Na+].[Na+].[CH2:18]([C:20]([C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([CH3:46])[CH:40]=1)([C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[C:25]([CH3:38])[CH:24]=1)[CH2:21][CH3:22])[CH3:19].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:10][O:9][C:7]([C:5]1[S:6][C:2]([C:26]2[CH:27]=[CH:28][C:23]([C:20]([CH2:21][CH3:22])([C:39]3[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([CH3:46])[CH:40]=3)[CH2:18][CH3:19])=[CH:24][C:25]=2[CH3:38])=[C:3]([CH3:11])[CH:4]=1)=[O:8]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2795489Methyl 5-bromo-4-methylthiophene-2-carboxylateHCID 577091704-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol

生成物 1

HCID 574434855-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-4-methyl-thiophene-2-carboxylic Acid Methyl Ester収率 46.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
85 °C

実験手順

Methyl 5-bromo-4-methyl-2-thiophenecarboxylate (178.85 mg, 0.761 mmol), tetrakistriphenylphosphine palladium (14.7 mg, 0.013 mmol) and a 2 M sodium carbonate aqueous solution (0.3 mL, 0.6 mmol) were added to a solution of 4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 15-(2); 100 mg, 0.254 mmol) in toluene (0.5 mL) at room temperature, and the mixture was stirred at 85° C. for 17 hours. Ethyl acetate was added to the reaction solution. The organic layer was filtered through celite, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound (50.3 mg, 46.9%).

後処理

  1. filtrationThe organic layer was filtered through celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-9c0370da1bdb425ba0d2a700dfd6e3fd
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

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