Water → 2-(3-Bromo-4-methoxy-phenyl)-propionic acid ethyl ester

HRID 1773957ノート

反応式

HRID 1773957 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([Br:14])[CH:7]=1)[CH3:2].[H-].[Na+].I[CH3:19].O>C1COCC1>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([Br:14])[CH:7]=1)[CH3:19])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57419861Ethyl 3-bromo-4-methoxyphenylacetate

生成物 1

HCID 574588042-(3-Bromo-4-methoxy-phenyl)-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice-cooled solution of (3-bromo-4-methoxy-phenyl)-acetic acid ethyl ester (1.45 g, 5.12 mmol, 1.00 eq.) in THF (18 mL), sodium hydride (60% dispersion in mineral oil, 225 mg, 5.63 mmol, 1.10 eq.) was added. The reaction mixture was stirred at r.t. for 30 min. Iodomethane (0.34 mL, 5.38 mmol, 1.05 eq.) was added and the resulting mixture was stirred at r.t. for 18 hours. Water was carefully added. THF was removed in vacuo. The residue was extracted with AcOEt (2×). The org. layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flashmaster (column: 50 g, flow: 40 mL/min, 25 fractions of 40 mL, Heptane 100% to Heptane+15% AcOEt) to yield the title compound as a yellow oil.

後処理

  1. additionwas added
  2. stirringthe resulting mixture was stirred at r.t. for 18 hours
  3. customTHF was removed in vacuo
  4. extractionThe residue was extracted with AcOEt (2×)
  5. dry with materiallayer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flashmaster (column: 50 g, flow: 40 mL/min, 25 fractions of 40 mL, Heptane 100% to Heptane+15% AcOEt)

出典と根拠

ORDレコード
ord-d115bbc2b9a24125b417c3666733d880
出典データセット
uspto-grants-2016_02
特許番号
US09255090B2

反応ノート

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