3-Tert-butoxymethyl-4-fluoro-3-hydroxybutyric acid tert-butyl ester → 4-Fluoromethyl-4-hydroxy-dihydro-furan-2-one

HRID 1436921Notes

Reaction equation

HRID 1436921 reaction equation
C(O[C:6](=[O:18])[CH2:7][C:8]([CH2:12][O:13]C(C)(C)C)([OH:11])[CH2:9][F:10])(C)(C)C>FC(F)(F)C(O)=O>[F:10][CH2:9][C:8]1([OH:11])[CH2:12][O:13][C:6](=[O:18])[CH2:7]1

Participants

3

Reactant 1

HCID 579396953-Tert-butoxymethyl-4-fluoro-3-hydroxybutyric acid tert-butyl ester

Product 1

HCID 579396974-Fluoromethyl-4-hydroxy-dihydro-furan-2-oneYield 96.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 17.47 g crude 3-tert-butoxymethyl-4-fluoro-3-hydroxybutyric acid tert-butyl ester (from 64.85 mmol 1-tert-butoxy-3-fluoro-propan-2-one) in 20 mL trifluoroacetic acid was stirred at 40° C. for 30 min. The resulting brown solution was evaporated and the residue subjected to bulb-to-bulb distillation at 150-160° C./0.4 mbar to provide 8.40 g (96.6% from 1-tert-butoxy-3-fluoro-propan-2-one) 4-fluoromethyl-4-hydroxy-dihydro-furan-2-one as yellow oil. 1H-NMR (CDCl3, 300 MHz): 4.46 (d, J=47, CH2F); 4.33 (AB with fine structure, J=10 and 2, —CH2—O); 3.33 (s br, OH); 2.70 (AB with fine structure, J=18, —CH2—C(O)).

Workup

  1. customThe resulting brown solution was evaporated
  2. distillationthe residue subjected to bulb-to-bulb distillation at 150-160° C./0.4 mbar

Sources & evidence

ORD record
ord-075f935aaef74c9c9f6f1313f39027d1
Source dataset
uspto-grants-2009_11
Patent number
US07619101B2

Reaction notes

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