Triphenylphosphine → 3-[2-(4-(2-Methyl-1,3-dioxolan-2-ylmethoxy)phenoxy)ethyl]-5-(phenoxymethyl)oxazolidin-2-one

HRID 2082081Notes

Reaction equation

HRID 2082081 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][C:14]1([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[O:18][CH2:17][CH2:16][O:15]1.[O:28]([CH2:35][CH:36]1[O:40][C:39](=[O:41])[N:38]([CH2:42][CH2:43]O)[CH2:37]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:13][C:14]1([CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:43][CH2:42][N:38]3[CH2:37][CH:36]([CH2:35][O:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:40][C:39]3=[O:41])=[CH:23][CH:22]=2)[O:18][CH2:17][CH2:16][O:15]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 197795284-[(2-Methyl-1,3-dioxolan-2-yl)methoxy]phenolHCID 19779529HCID 19779529, compound

Product 1

HCID 197795303-[2-(4-(2-Methyl-1,3-dioxolan-2-ylmethoxy)phenoxy)ethyl]-5-(phenoxymethyl)oxazolidin-2-oneYield 62.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.6 ml) was added dropwise to an ice-bath cooled, stirred, solution of 4-[(2-methyl-1,3-dioxolan-2-yl)methoxy]phenol (2.1 g), 5-phenoxymethyl-3-(2-hydroxyethyl)-oxazolidin-2-one (2.4 g) and triphenylphosphine (2.6 g) in anhydrous tetrahydrofuran (50 ml) under argon. The reaction mixture was left for 64 hours at 22° C. and then the solvent removed under reduced pressure. The residue was dissolved in dichloromethane and the solution seeded with 1,2-dicarbethoxyhydrazine. The solution was allowed to stand for 2 hours, the solid was collected and the filtrate was subjected to chromatography using 45% hexane in ethyl acetate grading to 40% hexane in ethyl acetate as eluent. The appropriate fractions were combined, evaporated, and the residue triturated with cyclohexane to give the 3-[2-(4-(2-methyl-1,3-dioxolan-2-ylmethoxy)phenoxy)ethyl]-5-(phenoxymethyl)oxazolidin-2-one (2.7 g) m.p. 75°-77° C.

Workup

  1. temperaturecooled
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. waitto stand for 2 hours
  5. customthe solid was collected
  6. customevaporated
  7. customthe residue triturated with cyclohexane

Sources & evidence

ORD record
ord-3ba6c872cf384304a9411ce5751ad339
Source dataset
uspto-grants-1993_02
Patent number
US05187190

Reaction notes

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