Water → Methyl 4-([1,1'-biphenyl]-3-ylmethoxy)benzenepropanoate

HRID 1678567ノート

反応式

HRID 1678567 の反応式
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.B([O-])O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C(CO)=CC=CC=1.O>[C:2]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoateHCID 178514829HCID 178514829、化合物

生成物 1

HCID 23082944Methyl 4-([1,1'-biphenyl]-3-ylmethoxy)benzenepropanoate収率 93.4%

試薬・触媒・溶媒 1

HCID 66808090HCID 66808090、化合物溶媒

実験手順

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.60 g, 1.7 mmol), phenyl boronate (0.25 g, 2.1 mmol) and sodium carbonate (0.55 g, 5.2 mmol) were dissolved in toluene-methanol-water (5:1:1, 35 mL), the mixture was purged with argon, and then tetrakistriphenylphosphine palladium (99 mg, 0.086 mmol) was added thereto. The reaction solution was heated under reflux overnight under argon atmosphere. The reaction solution was cooled, and then water was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with water, dried and then concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.55 g, yield 92%) as white powders.

後処理

  1. customthe mixture was purged with argon
  2. temperatureThe reaction solution was heated
  3. temperatureunder reflux overnight under argon atmosphere
  4. temperatureThe reaction solution was cooled
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1)

出典と根拠

ORDレコード
ord-0b4f74c77ac3488fa3fa43aa98fc548c
出典データセット
uspto-grants-2011_08
特許番号
US08008525B2

反応ノート

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