2-Oxazolidinone, 3-(2-hydroxyethyl)- → HCID 22154941, compound

HRID 2244119Notes

Reaction equation

HRID 2244119 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31]>ClCCl>[O:31]=[C:27]1[N:26]([CH2:25][CH:24]=[O:23])[CH2:30][CH2:29][O:28]1

Participants

4

Reactant 2

HCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-HCID 159087Triacetoxyperiodinane

Product 1

HCID 22154941HCID 22154941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A Dess-Martin reagent (516 mg) was added to a solution of 3-(2-hydroxyethyl)oxazolidin-2-one (144 mg) in dichloromethane (5.0 ml), and the mixture was stirred for 1 hour at room temperature. The solvent was evaporated off to obtain crude crystals, (2-oxooxazolidin-3-yl)acetaldehyde without purification. A solution of ammonium acetate (771 mg) in methanol (5.0 ml) was added to a suspension of (2-oxooxazolidin-3-yl)acetaldehyde and Compound 204 (286 mg) in tetrahydrofuran (10 ml), and the mixture was stirred for 2 weeks at room temperature. The reaction solution was neutralized with a saturated aqueous solution of sodium hydrogen carbonate and then extracted twice with ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated. The residue was purified by NH silica gel column chromatography (chloroform→chloroform:methanol=95:5) and then recrystallized (methanol-ethyl acetate-hexane) to yield the title compound (149 mg) as a colorless powder (mp: 232.0-233.0° C.)

Workup

  1. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-7e0bff246a274499b9a02ad555113417
Source dataset
uspto-grants-2010_03
Patent number
US07678810B2

Reaction notes

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