HCID 66912107, compound → HCID 58706352, compound

HRID 1990857Notes

Reaction equation

HRID 1990857 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[NH:10][C:11](=[O:13])[O:12][C:8]=2[CH:7]=[C:6]([CH2:14][OH:15])[CH:5]=1)[CH3:2]>ClCCl.C(O)C.O=[Mn]=O>[CH2:1]([O:3][C:4]1[C:9]2[NH:10][C:11](=[O:13])[O:12][C:8]=2[CH:7]=[C:6]([CH:14]=[O:15])[CH:5]=1)[CH3:2]

Participants

5

Reactant 1

HCID 66912107HCID 66912107, compound

Product 1

HCID 58706352HCID 58706352, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 4-ethoxy-6-hydroxymethyl-3H-benzooxazol-2-one (0.69 g, 3.30 mmol, 1.0 equiv) in a mixture of dichloromethane (40 mL) and ethanol (5 mL) was added activated MnO2 (1.15 g, 13.2 mmol, 4.0 equiv). The reaction mixture was heated to 40° C. for 2 h, filtered through Hyflo Super Cel and concentrated by evaporation under reduced pressure. The residue was purified by flash column chromatography on silica eluting with heptane/ethyl acetate (1:1) to yield 0.53 g (78% yield) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.43 (t, J=7.0 Hz, 3H), 4.23 (q, J=7.0 Hz, 2H), 7.38 (s, 1H), 7.42 (s, 1H), 9.87 (s, 1H), 12.28 (br s, 1H). 13C NMR (75 MHz, DMSO): δ 14.41, 64.63, 104.07, 109.32, 125.20, 131.05, 143.13, 143.88, 154.21, 191.11. MS (ISP): 208.1 [M+H]+.

Workup

  1. filtrationfiltered through Hyflo Super Cel
  2. concentrationconcentrated by evaporation under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica eluting with heptane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-25a9f49001f44827b8a98a31e363cd59
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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