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

HRID 1172887Notes

Reaction equation

HRID 1172887 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4410efe3f1ae4707880276c52f8e5d7f
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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