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

반응식

HRID 546838 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
85 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-9c0370da1bdb425ba0d2a700dfd6e3fd
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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