Diethyl Ether → HCID 67419590, compound

HRID 915194Notes

Reaction equation

HRID 915194 reaction equation
[CH3:1]COCC.CC(C)([O-])C.[K+].C(OCC[O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26][CH2:27][C:28]2[N:29]=[C:30]([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:37]=3[Cl:43])[O:31][C:32]=2[CH:33]([CH3:35])[CH3:34])=[CH:21][C:20]=1[CH3:45])(=O)C.[C:46]([O:49][CH2:50][CH3:51])(=[O:48])[CH3:47]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:43][C:37]1[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:36]=1[C:30]1[O:31][C:32]([CH:33]([CH3:34])[CH3:35])=[C:28]([CH2:27][CH2:26][C:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:47][C:46]([O:49][CH2:50][CH3:51])=[O:48])=[C:20]([CH3:45])[CH:21]=2)=[CH2:1])[N:29]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether3×HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxide2×HCID 67418872HCID 67418872, compound

Product 1

HCID 67419590HCID 67419590, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst2×

Procedure

In a dry ether (2 mL), potassium t-butoxide (120 mg, 1.07 mmol) was suspended. Methyl triphenyl phosphonium bromide (350 mg, 0.98 mmol) was added to the suspension. The mixture was stirred for 2 hours at room temperature. [4-[3-[2-(2,4-dichlorophenyl)-5-isopropyl-4-oxazolyl]propionyl]-2-methylphenoxy]ethyl acetate (450 mg, 0.89 mmol) and a dry ether (1.5 mL) were added to the mixture. The resulting mixture was stirred for 16 hours at room temperature. Methyl triphenyl phosphonium bromide (175 mg, 0.49 mmol), a dry ether (5 mL) and potassium t-butoxide (60 mg, 0.53 mmol) were added to the reaction mixture. The resulting mixture was stirred for 30 minutes at room temperature. The mixture was refluxed for 4 hours, and allowed to room temperature. Ethyl acetate (10 mL) was added to the reaction mixture. The mixture was washed with water (10 mL), and a saturated saline (10 mL), and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel with ethyl acetate/hexane (1/9) to give the desired compound (131 g) as colorless oil (yield 29%).

Workup

  1. stirringThe resulting mixture was stirred for 16 hours at room temperature
  2. stirringThe resulting mixture was stirred for 30 minutes at room temperature
  3. temperatureThe mixture was refluxed for 4 hours
  4. customallowed to room temperature
  5. washThe mixture was washed with water (10 mL)
  6. dry with materiala saturated saline (10 mL), and dried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel with ethyl acetate/hexane (1/9)

Sources & evidence

ORD record
ord-a9f2e1822ea44ae29e72462102d6af0b
Source dataset
uspto-grants-2007_09
Patent number
US07265137B2

Reaction notes

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