Tert-Butyl hypochlorite → HCID 86714591, compound

HRID 1025930Notes

Reaction equation

HRID 1025930 reaction equation
[Br: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>[Br:1][CH2:2][C:3]1([CH3:9])[CH2:7][O:6][C:5](=[O:8])[N:4]1[Cl:15]

Participants

4

Reactant 2

HCID 521297Tert-Butyl hypochloriteHCID 86714590HCID 86714590, compound

Product 1

HCID 86714591HCID 86714591, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(bromomethyl)-4-methyloxazolidin-2-one (1.33 g, 6.86 mmol) in MeOH (10 ml) was cooled to 0° C. and tert-butylhypochlorite (1.0 ml, 8.4 mmol) as added dropwise. The solution was stirred for 30 min, concentrated in vacuo, and the residue purified by flash chromatography (20% to 60% ethyl acetate in hexanes) to afford the title compound as a white solid (960 mg, 4.20 mmol, 61%). 1H NMR (CDCl3, 400 MHz) δ 1.57 (s, 3H), 3.45 (d, J=10.4 Hz, 1H), 3.60 (d, J=10.8 Hz, 1H), 4.20 (d, J=8.8 Hz, 1H), 4.51 (d, J=8.8 Hz, 1H). LRMS (ESI/APCI): 228 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by flash chromatography (20% to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-939d1a18b9714e088b36ef9a4efcc2da
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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