Trifluoroacetic acid → HCID 70979320, compound

HRID 1485406Notes

Reaction equation

HRID 1485406 reaction equation
C(O)(C(F)(F)F)=O.[C:8]1([C:23]([O:25]C(C)(C)C)=[O:24])([C:16]([O:18]C(C)(C)C)=[O:17])[CH2:10][CH:9]1[C:11]([O:13][CH2:14][CH3:15])=[O:12]>ClCCl>[CH2:14]([O:13][C:11]([CH:9]1[CH2:10][C:8]1([C:23]([OH:25])=[O:24])[C:16]([OH:18])=[O:17])=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70978401HCID 70978401, compound

Product 1

HCID 70979320HCID 70979320, compoundYield 123.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (4.5 g, 39.7 mmol) was added into a solution of 1,1-di-tert-butyl 2-ethyl cyclopropane-1,1,2-tricarboxylate (4.9 g, 13.2 mmol) in dichloromethane (20 mL) and the mixture was stirred at room temperature for 48 h. The solvent was evaporated in vacuo and the excess TFA was lyophilized to afford 2-(ethoxycarbonyl)cyclopropane-1,1-dicarboxylic acid (3.3 g, 100%). 1H NMR (300 MHz, CD3OD): δ 1.23-1.29 (t, J=6.9 Hz, 3H), 1.60-1.64 (m, 1H), 1.85-1.88 (m, 1H), 2.48-2.53 (m, 1H), 4.10-4.18 (m, 1H).

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-90dab36b1d6c4d1bb5d0426fe7452d65
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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