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

HRID 1172879

Reaction equation

HRID 1172879 reaction equation
C([O:5][C:6](=[O:29])[CH:7]([C:15]1[CH:28]=[CH:27][C:18]2[CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:17]=2[CH:16]=1)[C:8]([O:10]C(C)(C)C)=[O:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:25]([O:24][C:22]([C:20]1[S:21][C:17]2[CH:16]=[C:15]([CH:7]([C:8]([OH:10])=[O:9])[C:6]([OH:29])=[O:5])[CH:28]=[CH:27][C:18]=2[CH:19]=1)=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59424236Di-tert-butyl [2-(ethoxycarbonyl)-1-benzothien-6-yl]malonate

Product 1

HCID 59424242[2-(Ethoxycarbonyl)-1-benzothien-6-yl]malonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-tert-butyl[2-(ethoxycarbonyl)-1-benzothien-6-yl]malonate (0.873 g, 2.08 mmol) was dissolved in DCM (5 mL) and TFA (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 (white solid). 1H NMR (DMSO-d6) δ 13.10 (br s, 2H), 8.17 (s, 1H), 8.03 (s, 1H), 7.98 (d, J=8.4 Hz, 1H), 7.47 (dd, J=8.4, 1.8 Hz, 1H), 4.83 (s, 1H), 4.33 (q, J=7.2 Hz, 2H), 1.32 (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 (white solid)

Sources & evidence

ORD record
ord-8067dd964e7242a0977b5bc68225919a
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Linked notes

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