Boron trifluoride etherate → (1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650403ノート

反応式

HRID 650403 の反応式
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)=[C:11]3[C:28]([O:30]CC)=[O:29])=[CH:4][C:3]=2[O:2]1.C1OC2C=CC(C3(O)C4C(=CC=CC=4)C(C4C=CC5OCOC=5C=4)=C3C(OCC)=O)=CC=2O1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)[CH:11]3[C:28]([OH:30])=[O:29])=[CH:4][C:3]=2[O:2]1

参加物

6

反応物 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 21714780Ethyl (RS)-1,3-Di-(3,4-methylenedioxyphenyl)indene-2-carboxylateHCID 21714787Ethyl (1RS)-1,3-di-(3,4-methylenedioxyphenyl)-1-hydroxyindene-2-carboxylate

生成物 1

HCID 10135727(1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid収率 92%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl(RS)-1,3-Di-(3,4-methylenedioxyphenyl)indene-2-carboxylate. To a solution of ethyl (1RS)-1,3-di-(3,4-methylenedioxyphenyl)-1-hydroxyindene-2-carboxylate (0.29 g, 0.65 mmol) in CH2Cl2 (3 ml) at 0° C. under an argon atmosphere was added triethylsilane (91 mg, 0.78 mmol), followed by boron trifluoride etherate (0.3 ml, 2.4 mmol). The reaction mixture was stirred for 10 min, at which time was added ice-cold 1M HCl, and the mixture was extracted with EtOAc. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was placed on a small pad of silica gel, eluting with CH2CL2 to provide the title compound (257 mg, 92%).

後処理

  1. extractionthe mixture was extracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. washeluting with CH2CL2

出典と根拠

ORDレコード
ord-742ab58602f24030b440f849bc542aee
出典データセット
uspto-grants-2001_08
特許番号
US06271399B1

反応ノート

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