Benzyl Bromide → Methyl 2-(2-methoxyphenyl)-3-phenylpropanoate

HRID 509132

反応式

HRID 509132 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].C1COCC1.C([N-]C(C)C)(C)C.[Li+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCCCCCC.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:10]([O:12][CH3:13])=[O:11]

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 99590Methyl 2-methoxybenzeneacetateHCID 2724682Lithium diisopropylamide

生成物 1

HCID 66695010Methyl 2-(2-methoxyphenyl)-3-phenylpropanoate収率 35%

試薬・触媒・溶媒 1

HCID 21263495Tetrahydrofuran heptane溶媒

反応条件

温度
0 °C

実験手順

A 500 mL round-bottom flask is charged with methyl 2-(2-methoxyphenyl)acetate (8.496 g, 47 mmol, 1 eq) and THF (200 mL). The homogeneous mixture is cooled to 0° C. in an ice bath. Lithium diisopropyl amide (23.5 mL of a 2.0M solution in heptane/THF) is added, maintaining a temperature less than 3° C. The reaction is stirred 45 minutes at this reduced temperature. Benzyl bromide (5.6 mL, 47 mmol, 1 eq) is added dropwise. The reaction is allowed to gradually warm to room temperature and is stirred for 18 hours. The reaction is quenched with 1N HCl and extracted 3 times with equal portions of EtOAc. The combined extracts are washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The residue is purified over silica to afford 4.433 g (35%) of the desired compound. ESI+ MS 293 (M+Na).

後処理

  1. temperaturemaintaining a temperature less than 3° C
  2. temperatureto gradually warm to room temperature
  3. stirringis stirred for 18 hours
  4. customThe reaction is quenched with 1N HCl
  5. extractionextracted 3 times with equal portions of EtOAc
  6. washThe combined extracts are washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified over silica

出典と根拠

ORDレコード
ord-1d483272f4934cfc8eafd3af1892ec0c
出典データセット
uspto-grants-2015_08
特許番号
US09096555B2

関連ノート

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