Water → HCID 23371847, compound

HRID 1900071Notes

Reaction equation

HRID 1900071 reaction equation
[Br-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].[NH2-].[Na+].O=[C:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH2:43][CH:42]([CH2:44][O:45][CH3:46])[O:41][C:40]3=[O:47])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1.O>O1CCCC1>[CH3:46][O:45][CH2:44][CH:42]1[O:41][C:40](=[O:47])[N:39]([C:36]2[CH:37]=[CH:38][C:33]([CH:30]3[CH2:31][CH2:32][C:27](=[C:2]([CH3:4])[CH3:3])[CH2:28][CH2:29]3)=[CH:34][CH:35]=2)[CH2:43]1

Participants

5

Reactant 3

HCID 962WaterHCID 23371853HCID 23371853, compoundHCID 86749981Sodium triphenyl(propan-2-yl)phosphanium bromide azanide (1/1/1/1)

Product 1

HCID 23371847HCID 23371847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.60 g (3.3 mmol) of isopropyl-triphenylphosphonium bromide/sodium amide mixture in 30 ml of tetrahydrofuran were stirred at room temperature for 1 hour. Then, a solution of 1.0 g (3.3 mmol) of (RS)-3-[4-(4-oxo-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one in 25 ml of tetrahydrofuran was added dropwise. After boiling at reflux over the weekend the mixture was poured into 100 ml of water and extracted three times with 50 ml of dichloromethane each time. After chromatography over silica gel with ethyl acetate/hexane 1:2 and recrystallization from n-hexane 120 mg (11%) were obtained as white crystals with m.p. 89°-91°.

Workup

  1. temperatureat reflux over the weekend the mixture
  2. extractionextracted three times with 50 ml of dichloromethane each time
  3. customAfter chromatography over silica gel with ethyl acetate/hexane 1:2 and recrystallization from n-hexane 120 mg (11%)
  4. customwere obtained as white crystals with m.p. 89°-91°

Sources & evidence

ORD record
ord-4811b2ca53364e5b9f0d6591a07a6fd3
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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