Water → HCID 23371854, compound

HRID 1900059Notes

Reaction equation

HRID 1900059 reaction equation
[Br-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].O=[C:25]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:41][CH:40]([CH2:42][O:43][CH3:44])[O:39][C:38]3=[O:45])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.O>O1CCCC1>[CH3:44][O:43][CH2:42][CH:40]1[O:39][C:38](=[O:45])[N:37]([C:34]2[CH:35]=[CH:36][C:31]([CH:28]3[CH2:29][CH2:30][C:25](=[CH2:2])[CH2:26][CH2:27]3)=[CH:32][CH:33]=2)[CH2:41]1

Participants

5

Reactant 3

HCID 962WaterHCID 16212304Sodium;azanide;methyl(triphenyl)phosphanium;bromideHCID 23371853HCID 23371853, compound

Product 1

HCID 23371854HCID 23371854, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.76 g (13.8mmol) of methyltriphenylphosphonium bromide/sodium amide mixture were stirred at room temperature under argon in 170 ml of tetrahydrofuran for 1 hour. Then, a solution of 4.20 g (13.8 mmol) of (RS)-3-[4-(4-oxo-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one was added dropwise within 5 minutes. After boiling under reflux overnight the mixture was poured into water and extracted with methylene chloride. After drying with sodium sulfate and concentrating the residue was chromatographed over silica gel with ethyl acetate/n-hexane (1:2). 3.47 g (83%) of a solid were obtained. A small sample was recrystallized from hexane. M.p.: 63°-65°.

Workup

  1. temperatureunder reflux overnight the mixture
  2. extractionextracted with methylene chloride
  3. dry with materialAfter drying with sodium sulfate
  4. concentrationconcentrating the residue
  5. customwas chromatographed over silica gel with ethyl acetate/n-hexane (1:2)

Sources & evidence

ORD record
ord-f4092fd9a5bf429691e83a6801cdf5c8
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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