Water → HCID 23114209, compound

HRID 2376526Notes

Reaction equation

HRID 2376526 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:28]([C:31]1[CH:36]=[CH:35][C:34]([CH:37]2[C:41]3[C:42]([CH3:56])=[C:43]([NH:48][C:49](=[O:55])[CH2:50][C:51]([CH3:54])([CH3:53])[CH3:52])[C:44]([CH3:47])=[C:45]([CH3:46])[C:40]=3[O:39][CH2:38]2)=[CH:33][C:32]=1[O:57][CH3:58])(=O)[CH3:29].O>C1(C)C=CC=CC=1>[C:28]([C:31]1[CH:36]=[CH:35][C:34]([CH:37]2[C:41]3[C:42]([CH3:56])=[C:43]([NH:48][C:49](=[O:55])[CH2:50][C:51]([CH3:53])([CH3:54])[CH3:52])[C:44]([CH3:47])=[C:45]([CH3:46])[C:40]=3[O:39][CH2:38]2)=[CH:33][C:32]=1[O:57][CH3:58])([CH3:29])=[CH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 638159Methyltriphenylphosphonium iodideHCID 23114108HCID 23114108, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23114209HCID 23114209, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of potassium tert-butoxide (818 mg, 7.29 mmol) in toluene (45 mL) was added methyl triphenylphosphonium iodide (2.94 g, 7.29 mmol) and the resulting mixture was stirred at 120° C. for 1 hour under an argon atmosphere. To the reaction solution was added N-(3-(4-acetyl-3-methoxyphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (2.32 g, 5.48 mmol) obtained in Example 183 and the resulting mixture was stirred at 120° C. for 2 hours. Water was added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3) to obtain 1.93 g (yield: 84%) of the title compound. Melting point: 186-187° C. (ethyl acetate-hexane).

Workup

  1. stirringthe resulting mixture was stirred at 120° C. for 2 hours
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-80457674f9f44321b93bf56ea53157bf
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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