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Sodium hydride → 3-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester

HRID 1245394
Notes
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Reaction equation

HRID 1245394 reaction equation
COP([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(OC)=O.[H-].[Na+].[CH3:17][C:18]1[CH:27]=[C:26]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH2:40][CH:39]([CH:41]=O)[O:38][N:37]=3)=[CH:32][CH:31]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>CN(C=O)C>[C:11]([O:10][C:8](=[O:9])[CH:7]=[CH:41][CH:39]1[O:38][N:37]=[C:36]([C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:28][C:26]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[C:18]([CH3:17])[CH:27]=3)=[CH:31][CH:32]=2)[CH2:40]1)([CH3:12])([CH3:13])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4564495tert-Butyl DimethylphosphonoacetateHCID 218980783-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde

Product 1

HCID 696396783-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl esterYield 61.9%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

t-Butyl dimethylphosphonoacetate (0.31 g, 1.38 mmol) was added to a suspension of sodium hydride (washed with hexanes) (0.061 g @60%, 1.5 mmol) in DMF (3 mL) cooled in an ice bath, under a nitrogen atmosphere. The reaction was stirred for 0.5 h and the product from step 10b (0.31 g, 1.38 mmol) in DMF (3 mL) was added. The reaction was stirred for 2 h at 0° C. and was complete. This was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting methylene chloride:ethyl acetate (70:30) to give 3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester (0.38 g, 61%) as an oil. MS found: (M+H)+=445.

Workup

  1. temperaturecooled in an ice bath, under a nitrogen atmosphere
  2. stirringThe reaction was stirred for 2 h at 0° C.
  3. customThis was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe product was purified by FCC on silica gel
  9. washeluting methylene chloride:ethyl acetate (70:30)

Sources & evidence

ORD record
ord-e5ae2a6712374c82a15a87da5b33719f
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07125870B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes