Trifluoroacetic acid → HCID 86706152, compound

HRID 2176304Notes

Reaction equation

HRID 2176304 reaction equation
C([O:5][C:6]([C:8]1([CH:15]=[CH2:16])[CH2:13][O:12][C:11](=[O:14])[O:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[O:14]=[C:11]1[O:10][CH2:9][C:8]([CH:15]=[CH2:16])([C:6]([OH:7])=[O:5])[CH2:13][O:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86706151HCID 86706151, compound

Product 1

HCID 86706152HCID 86706152, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-oxo-5-vinyl-[1,3]dioxane-5-carboxylic acid tert-butyl ester (200 mg, 0.88 mmol) in dichloromethane (4 mL) was stirred at 0° C. Trifluoroacetic acid (2 mL) was added and the reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 3 h. The solvent was evaporated and the residue was triturated with diethyl ether/iso-hexanes (1:1) to afford the title compound (135 mg, 90%) as a white solid. 1H NMR (300 MHz, d6-DMSO) 64.51 (d, J=10.5 Hz, 2H), 4.67 (d, J=10.5 Hz, 2H), 5.38 (d, J=17.6 Hz, 1H), 5.43 (d, J=10.7 Hz, 1H), 5.83 (dd, J=17.6, 10.7 Hz, 1H), 13.5-14.0 (br s, 1H). LCMS (m/z) 173.2 [M+H], Tr=0.62 min.

Workup

  1. waitat room temperature for 3 h
  2. customThe solvent was evaporated
  3. customthe residue was triturated with diethyl ether/iso-hexanes (1:1)

Sources & evidence

ORD record
ord-dced32131b55481683ee32eced5cbc4e
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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