Ethanol → Methyl 3-(4-((2'-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422288

反応式

HRID 2422288 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1.[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(O)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)[CH:3]=1)[CH3:23]

参加物

7

反応物 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2734902(2-Ethoxyphenyl)boronic acidHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

生成物 1

HCID 23083192Methyl 3-(4-((2'-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate収率 63%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 3-[4-[(3-bromobenzyl)oxy]phenyl]propanoate (0.30 g, 0.86 mmol), 2-ethoxyphenylboronic acid (0.16 g, 0.95 mmol), tetrakistriphenylphosphine palladium (40 mg, 0.034 mmol), 2N potassium carbonate aqueous solution (0.3 mL), ethanol (0.3 mL) and toluene (3 mL) was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give methyl 3-(4-((2′-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate (0.21 g, 63%) as a colorless oil.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

出典と根拠

ORDレコード
ord-a3f0659dc5fd4a16ba8c2dbd58ae8010
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

関連ノート

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