Potassium Carbonate → 7-(2-(5-(3-Chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,5-dioxabenzocycloheptan-3-one

HRID 374893

Reaction equation

HRID 374893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:24])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:23])[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:26][C:27]([CH2:29]Br)=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:24])[CH2:15][CH:16]3[CH2:21][CH2:20][C:19]4[O:22][CH2:26][C:27](=[O:28])[CH2:29][C:18]=4[O:23][CH2:17]3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699521,3-Dibromo-2-propanoneHCID 156692045-(3-Chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

Product 1

HCID 189963407-(2-(5-(3-Chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,5-dioxabenzocycloheptan-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727 Example 1, is treated with one equivalent of 1,3-dibromoacetone and excess potassium carbonate in acetonitrile. The mixture is stirred at room temperature for 18 hours, filtered and evaporated in vacuo to give 7-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,5-dioxabenzocycloheptan-3-one. One equivalent of this ketone is reduced, at room temperature for one hour, with excess sodium borohydride in methyl alcohol. The reaction mixture is poured into water, made acidic with 1N hydrochloric acid and extracted with methylene chloride. The organic extracts are dried and evaporated in vacuo to give 7-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl-1,5-dioxabenzocycloheptan-3-ol. Hydrolysis with 2.5N sodium hydroxide gives the title compound.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-364c07cef4214d6f95543b5dfef1310b
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Linked notes

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