Ethanol → HCID 72475368, compound

HRID 916042Notes

Reaction equation

HRID 916042 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][C:11]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:12][C:13]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])([CH3:15])[CH3:14])[CH:5]=O.[ClH:30].[NH2:31][OH:32].[CH2:33](O)C>C(O)(=O)C>[Cl:30][C:8]1[CH:7]=[C:4]([C:5](=[N:31][OH:32])[CH3:33])[CH:3]=[CH:2][C:9]=1[CH2:10][C:11]([OH:29])([C:25]([F:27])([F:26])[F:28])[CH2:12][C:13]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 44435662HCID 44435662, compound

Product 1

HCID 72475368HCID 72475368, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

In a sealed tube, a mixture of 40 mg (0.09 mmol) of 3-chloro-4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]benzaldehyde and 9 mg (0.135 mmol) hydroxylamine hydrochloride in 1 mL of ethanol and 1 mL glacial acetic acid was heated to 70° C. After 2 days, the reaction was concentrated under a stream of nitrogen. The residue was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from hexanes and then chromatographed on silica gel eluting with hexanes-ethyl acetate (9:1) to provide 18 mg (45%) of the title compound as an oil that crystallized upon standing, m.p. 136° C.-138° C.

Workup

  1. concentrationthe reaction was concentrated under a stream of nitrogen
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from hexanes
  7. customchromatographed on silica gel eluting with hexanes-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-4a30bc1e6fd94a91b4a6784e4d4d886a
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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