Water → HCID 14971843, compound

HRID 2226537Notes

Reaction equation

HRID 2226537 reaction equation
C[NH:2]N.CC([Si](C)(C)[O:9][C:10]1[CH:11]=[C:12]([C:16](=O)[C:17](=[CH:35][N:36]([CH3:38])C)[C:18]2O[C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:22]=2)[CH:13]=[CH:14][CH:15]=1)(C)C.[OH2:42]>>[C:23]1([C:21]2[N:22]=[C:18]([C:17]3[C:16]([C:12]4[CH:11]=[C:10]([OH:9])[CH:15]=[CH:14][CH:13]=4)=[N:2][N:36]([CH3:38])[CH:35]=3)[O:42][C:20]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 53638579HCID 53638579, compound

Product 1

HCID 14971843HCID 14971843, compound

Procedure

N-Methyl hydrazine (2.5 mL, 46.6 mmol) was added dropwise to 1-[3-[(1,1-dimethylethyl)dimethylsiloxy]phenyl]-2-[(dimethylamino) methylene]-2-(4,5-diphenyl-2-oxazolyl)ethanone (20) (12 g, 22.8 mmol) and the mixture stirred for about 1 hour, diluted with water, and extracted with dichloromethane. The organic phase was concentrated, and the residue was taken up in THF (150 mL), and tetra-n-butylammonium fluoride (27.84 mL of 1M solution) added. The reaction mixture was stirred about 5 minutes, concentrated, diluted with 1N HCl, and extracted with dichloromethane. Separation by SiO2 chromatography, (elution with 75% ether/hexanes) and recyrstallization from dichloromethane/ether/hexanes gave 3-methyl 2.3 g, (25%), mp 186°-188° C. and 5-methyl 2.85 g (50%), mp 213°-215° C. both as white solids.

Workup

  1. extractionextracted with dichloromethane
  2. concentrationThe organic phase was concentrated
  3. additiontetra-n-butylammonium fluoride (27.84 mL of 1M solution) added
  4. stirringThe reaction mixture was stirred about 5 minutes
  5. concentrationconcentrated
  6. additiondiluted with 1N HCl
  7. extractionextracted with dichloromethane
  8. customSeparation
  9. washby SiO2 chromatography, (elution with 75% ether/hexanes) and recyrstallization from dichloromethane/ether/hexanes
  10. customgave 3-methyl 2.3 g, (25%), mp 186°-188° C. and 5-methyl 2.85 g (50%), mp 213°-215° C. both as white solids

Sources & evidence

ORD record
ord-e58df5244e474da5951367f55c78e98a
Source dataset
uspto-grants-1994_09
Patent number
US05348969

Reaction notes

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