Hydrochloric Acid → (1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650753ノート

反応式

HRID 650753 の反応式
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]2[O:9][CH2:10][O:11][C:5]=2[CH:4]=1.C1OC2C=CC([Mg]Br)=CC=2O1.[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27]([C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34](=O)[C:33]=3[C:42]([O:44]CC)=[O:43])=[CH:26][C:25]=2[O:24]1.Cl>C1COCC1.CCOCC.C1COCC1>[CH2:10]1[O:9][C:6]2[CH:7]=[CH:8][C:3]([CH:34]3[C:35]4[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:32]([C:27]4[CH:28]=[CH:29][C:30]5[O:31][CH2:23][O:24][C:25]=5[CH:26]=4)[CH:33]3[C:42]([OH:44])=[O:43])=[CH:4][C:5]=2[O:11]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 5462224MagnesiumHCID 18427631Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylateHCID 178419615HCID 178419615、化合物

生成物 1

HCID 10135727(1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid収率 42%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21868444Ether tetrahydrofuran溶媒2 回

実験手順

To dry magnesium turnings (0.25 g, 10 mmol) under an argon atmosphere was added a solution of 4-bromo-1,2-methylenedioxybenzene (2.1 g, 10 mmnol) in 1:10 THF/Et2O (22 ml). The resulting solution was allowed to stir at room temperature for 2 h. During this time, additional THF (4 ml) was added. The resulting 3,4-methylenedioxyphenylmagnesium bromide was added to a solution of ethyl 3-(3,4-methylenedioxyphenyl)-1-oxoindene-2-carboxylate (0.50 g, 2 mmol) in 1:4 THF/Et2O (25 ml) under an argon atmosphere at 0° C. The resulting mixture was stirred at 0° C. for 15 min, at which time 1M HCl (50 ml) was added. The phases were separated and the aqueous phase was extracted with Et2O. The combined organic extracts were washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 10% EtOAc/hexanes to afford the title compound as a yellow solid (0.29 g, 42%).

後処理

  1. additionwas added
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with Et2O
  4. washThe combined organic extracts were washed with saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with 10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-e73d5794aec74cf6b4503ef2dd146fbb
出典データセット
uspto-grants-2001_08
特許番号
US06274737B1

反応ノート

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