Sulfuric Acid → Ethyl 7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

HRID 1868760ノート

反応式

HRID 1868760 の反応式
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Br:20][C:21]1[CH:22]=[C:23]([C:27]([CH3:42])([CH3:41])[C:28]([CH:30]([C:36](OCC)=[O:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29])[CH:24]=[CH:25][CH:26]=1>>[Br:20][C:21]1[CH:22]=[C:23]2[C:24]([C:36]([OH:37])=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:28](=[O:29])[C:27]2([CH3:41])[CH3:42])=[CH:25][CH:26]=1

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099417Diethyl 2-(2-(3-bromophenyl)-2-methylpropanoyl)malonate

生成物 1

HCID 67099405Ethyl 7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate収率 41.1%

実験手順

H2SO4 (60 mL, 710 mmol) was cooled to 0° C. and treated with P2O5 (20 g, 141 mmol). The mixture was brought to room temperature and added to diethyl 2-(2-(3-bromophenyl)-2-methylpropanoyl)malonate (17.44 g, 45 mmol). The reaction mixture was then stirred for 2 hours. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (3×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as an orange oil. The crude oil was purified by silica flash chromatography (0-100% DCM/hexane) to give the desired compound as a white solid (6.27 g). MS (m/e)=339.1 (M+H)+.

後処理

  1. customwas brought to room temperature
  2. additionIce (H2O) was added
  3. extractionthe aqueous mixture was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with water (2×) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give the crude compound as an orange oil
  8. customThe crude oil was purified by silica flash chromatography (0-100% DCM/hexane)

出典と根拠

ORDレコード
ord-9729967047bd4d7ab3750a5c9cf864b3
出典データセット
uspto-grants-2009_12
特許番号
US07635715B2

反応ノート

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