Tert-Butyl hypochlorite → HCID 53359810, compound

HRID 1025935Notes

Reaction equation

HRID 1025935 reaction equation
[F:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[NH:4]1.C(O[Cl:15])(C)(C)C>CO>[Cl:15][N:4]1[C:3]([CH2:2][F:1])([CH3:9])[CH2:7][O:6][C:5]1=[O:8]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 86714594HCID 86714594, compound

Product 1

HCID 53359810HCID 53359810, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(fluoromethyl)-4-methyloxazolidin-2-one (245 mg, 1.82 mmol) in MeOH (5 ml) was cooled to 0° C. and tert-butylhypochlorite (251 mg, 2.3 mmol) was added dropwise. The solution was stirred for 2 h, concentrated in vacuo, and the residue purified by flash chromatography (0% to 10% MeOH in DCM) to afford the title compound as a white solid (303 mg, 100%). 1H NMR (CDCl3, 400 MHz) δ 1.38 (d, J=2.4 Hz, 3H), 4.22 (dd, J=1.2, 8.8 Hz), 1H), 4.24 (d, J=11.2 Hz, 0.5H), 4.35 (d, J=10.4 Hz, 0.5H), 4.53 (d, J=10.4 Hz, 0.5H), 4.54 (dd, J=0.8, 8.8 Hz, 1H), 4.64 (d, J=10.4 Hz, 0.5H). 19F NMR (CDCl3, 376 MHz) δ −228.4 (t, J=84 Hz). 13C NMR (CDCl3, 100 MHz) δ 17.7 (d, J=3.7 Hz), 63.5 (d, J=18 Hz), 70.7 (d, J=4 Hz), 82 (d, J=179 Hz), 155.8 (s). LRMS (ESI/APCI): 168 [M+H]+, 209 [M+H+CH3CN]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography (0% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-38f0e286cfd04148a94ed3f885f11cab
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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