Potassium Carbonate → (R*,S*)-6-[5-(3-Chlorophenyl)-2-oxo-3-oxazolidinyl]-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-2,2-dicarboxylic acid diethyl ester

HRID 233817

Reaction equation

HRID 233817 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][C:18]([OH:25])=[C:19]([OH:24])[CH:20]=4)[CH2:15]3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[C:27](Br)([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:36]([O:35][C:33]([C:27]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[O:24][C:19]2[CH:20]=[C:21]3[C:16](=[CH:17][C:18]=2[O:25]1)[CH2:15][C@H:14]([N:10]1[CH2:9][C@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][C:11]1=[O:13])[CH2:23][CH2:22]3)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl esterHCID 233581385-(3-Chlorophenyl)-3-(1,2,3,4-tetrahydro-6,7-dihydroxynaphthalen-2-yl)-2-oxazolidinone

Product 1

HCID 67619602(R*,S*)-6-[5-(3-Chlorophenyl)-2-oxo-3-oxazolidinyl]-5,6,7,8-tetrahydronaphtho[2,3-d]-1,3-dioxole-2,2-dicarboxylic acid diethyl esterYield 54.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.90 g of the above catechol derivative, 0.836 g of diethyl dibromomalonate and 1.8 g of powdered anhydrous potassium carbonate in 15 ml of acetone is stirred at room temperature for 18 hours. The reaction mixture is filtered and concentrated in vacuo to give 0.708 g of a mixture of diastereomers as a colorless oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc06d8aa44f343808aff8578f99d8340
Source dataset
uspto-grants-1997_01
Patent number
US05594027

Linked notes

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