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

HRID 1172887노트

반응식

HRID 1172887 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4410efe3f1ae4707880276c52f8e5d7f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834034B2

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