Ethyl Acetate → HCID 66578520, compound

HRID 1528849Notes

Reaction equation

HRID 1528849 reaction equation
[Br-].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH3:14])[C:10]=2[CH2:15][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[C:41]1([CH:47]([CH3:51])[CH2:48][CH:49]=O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.CCOC(C)=O>C1COCC1>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([CH3:14])[C:10]=2[CH:15]=[CH:49][CH2:48][CH:47]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH3:51])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 859793-PhenylbutanalHCID 23665647Potassium tert-butoxideHCID 86673638HCID 86673638, compound

Product 1

HCID 66578520HCID 66578520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-triphenyl-phosphonium bromide (0.2678 g, 0.451 mmol) was dissolved in THF (2.7 mL) at 0° C. Potassium tert-butoxide (1 M in THF, 0.5 mL, 0.50 mmol) was added and after stirring 15 minutes 3-phenyl-butyraldehyde (0.074 mL, 0.50 mmol) was added and the ice bath was removed. After 15 minutes, analytical LCMS indicated complete reaction. Standard aqueous workup followed by silica gel chromatography (0-20% EtOAc in hexanes) afforded the title compound.

Workup

  1. additionwas added
  2. customthe ice bath was removed
  3. customreaction

Sources & evidence

ORD record
ord-901fe932868b4fe1a2405ea4904b388d
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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