Trifluoroacetic acid → [2-(Ethoxycarbonyl)-1-benzothien-6-yl](methyl)malonic acid

HRID 1172887ノート

反応式

HRID 1172887 の反応式
C([O:5][C:6](=[O:30])[C:7]([C:16]1[CH:29]=[CH:28][C:19]2[CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:22][C:18]=2[CH:17]=1)([CH3:15])[C:8]([O:10]C(C)(C)C)=[O:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:26]([O:25][C:23]([C:21]1[S:22][C:18]2[CH:17]=[C:16]([C:7]([CH3:15])([C:8]([OH:10])=[O:9])[C:6]([OH:30])=[O:5])[CH:29]=[CH:28][C:19]=2[CH:20]=1)=[O:24])[CH3:27]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 59424240Di-tert-butyl [2-(ethoxycarbonyl)-1-benzothien-6-yl](methyl)malonate

生成物 1

HCID 59424235[2-(Ethoxycarbonyl)-1-benzothien-6-yl](methyl)malonic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Di-tert-butyl[2-(ethoxycarbonyl)-1-benzothien-6-yl](methyl)malonate (0.26 g, 0.598 mmol) was dissolved in DCM (1.5 mL) and TFA (1.5 mL) was added. The solution was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue partitioned between saturated NaHCO3-EtOAc. The aqueous phase was acidified with 2N HCl and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give the product (pale yellow solid). 1H NMR (DMSO-d6) δ 13.12 (br s, 2H), 8.14 (s, 1H), 8.03 (d, J=1.8 Hz, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.47 (dd, J=8.4, 1.8 Hz, 1H), 4.32 (q, J=7.2 Hz, 2H), 1.77 (s, 3H), 1.31 (t, J=7.2 Hz. 3H).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between saturated NaHCO3-EtOAc
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the product (pale yellow solid)

出典と根拠

ORDレコード
ord-4410efe3f1ae4707880276c52f8e5d7f
出典データセット
uspto-grants-2010_11
特許番号
US07834034B2

反応ノート

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