Tributyl(3,3-dimethylbut-1-en-1-yl)stannane → (E)-Ethyl 5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxylate

HRID 1478176Notes

Reaction equation

HRID 1478176 reaction equation
C([Sn](CCCC)(CCCC)/[CH:6]=[CH:7]/[C:8]([CH3:11])([CH3:10])[CH3:9])CCC.Br[C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]=1[CH3:31]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:8]([CH3:9])([CH3:10])/[CH:7]=[CH:6]/[C:21]1[O:25][N:24]=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]=1[CH3:31]

Participants

5

Reactant 2

HCID 10948728Tributyl(3,3-dimethylbut-1-en-1-yl)stannaneHCID 58828802Ethyl 5-bromo-4-methyl-1,2-oxazole-3-carboxylate2×

Product 1

HCID 131736501(E)-Ethyl 5-(3,3-dimethylbut-1-en-1-yl)-4-methylisoxazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(E)-Tributyl(3,3-dimethylbut-1-en-1-yl)stannane (1194 mg, 0.8 mmol) and ethyl 5-bromo-4-methylisoxazole-3-carboxylate (Intermediate A) (187 mg, 0.8 mmol) were dissolved in dioxane (6 mL) and the mixture was degassed thoroughly, refilling with nitrogen. Pd(Ph3P)4 (92 mg, 0.080 mmol) was added and the mixture was stirred at 100° C. for 16 hours. The crude reaction mixture was adsorbed onto silica and purification by chromatography eluting with 0-10% EtOAc in iso-hexane afforded the title compound;

Workup

  1. customthe mixture was degassed thoroughly
  2. customThe crude reaction mixture
  3. customwas adsorbed onto silica and purification by chromatography
  4. washeluting with 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-b7830f39f1214ff6b9e9ada99ad7c4ae
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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