Bromide ion → HCID 58424695、化合物

HRID 1408813ノート

反応式

HRID 1408813 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2=[O:18].[Br-].[CH2:20]1COC[CH2:21]1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:5]2([CH:20]=[CH2:21])[OH:18]

参加物

4

反応物 3

HCID 259Bromide ionHCID 8028Tetrahydrofuran2 回HCID 52705456-Bromoflavanone

生成物 1

HCID 58424695HCID 58424695、化合物

実験手順

To a solution of 6-bromo-2-phenylchroman-4-one (2.021 g, 6.67 mmol) in anhydrous THF (35 mL) at −78° C. is added a solution of vinylmagnesiun bromide in THF (1 M, 10 mL, 10 mmol) dropwise within 30 min. The reaction temperature is allowed to warm to rt and stirred for another 2 h. The reaction is chilled to 0° C. and quenched with sat. aq. NH4Cl and extracted with ethyl acetate (2×40 mL). The combined organic phases are washed with H2O, brine, and dried over Na2SO4, and filtered. The filtrate is concentrated and the residue is purified through flash chromatography on silica gel to afford 6-bromo-2-phenyl-4-vinylchroman-4-ol as an oil (1.961 g. 89%). MS ESI+ve m/z 313 (M+H—H2O)+.

後処理

  1. temperatureThe reaction is chilled to 0° C.
  2. customquenched with sat. aq. NH4Cl
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe combined organic phases are washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. customthe residue is purified through flash chromatography on silica gel

出典と根拠

ORDレコード
ord-fee191639ad94c8e8386e64921d1cd2a
出典データセット
uspto-grants-2014_12
特許番号
US08921359B2

反応ノート

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