Potassium Carbonate → HCID 11514714, compound

HRID 2103033Notes

Reaction equation

HRID 2103033 reaction equation
[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:12](=[CH:13][C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[C:6]([CH:16]=[O:17])=[CH:5]2.S([CH2:29][N+:30]#[C-:31])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:18][C:3]1[C:2]([OH:1])=[C:14]([CH3:15])[CH:13]=[C:12]2[C:4]=1[CH:5]=[C:6]([C:16]1[O:17][CH:31]=[N:30][CH:29]=1)[C:7]1([O:11]2)[CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86605483HCID 86605483, compound

Product 1

HCID 11514714HCID 11514714, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde (315 mg), prepared as described herein, in 4 mL of MeOH was added tosylmethyl isocyanide (TosMIC) reagent (218 mg) and potassium carbonate (310 mg). The reaction mixture was allowed to heat at 80° C. for 20 min. The mixture was quenched with water and extracted with ethyl acetate. After concentrated in vacuo, the residue was purified by flash chromatography eluted with 30% ethyl acetate in hexane to give 118.8 mg of 5,7-dimethyl-3-(1,3-oxazol-5-yl)spiro[chromene-2,1′-cyclobutan]-6-ol as a yellow solid.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationAfter concentrated in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8a3a959aea6543d2b8d314cbef05f4cb
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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