Benzyl Bromide → Benzyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate

HRID 1667592ノート

反応式

HRID 1667592 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:15])[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:15])[C:12]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 138548502-(3,4-Dimethoxyphenyl)-2-hydroxyacetic acid

生成物 1

HCID 57448185Benzyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate収率 44.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To 6C (830 mg, 3.9 mmol) in DMF (15 mL) was added cesium carbonate (2.6 g, 8.0 mmol) followed by benzyl bromide (0.6 mL, 5 mmol). After stirring at rt overnight, the reaction was diluted with water, and was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-40% ethyl acetate/hexanes) to provide 6D (520 mg, 44%). LC-MS 445.31 (M+H)+.

後処理

  1. extractionwas extracted with ethyl acetate (2×30 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified via silica gel chromatography (0-40% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-589a4bbaff1b4154ac7e1a26908586dd
出典データセット
uspto-grants-2011_10
特許番号
US08044242B2

反応ノート

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