1,1'-(Diazomethylene)bis(benzene) → (2RS,3SR)-2-diphenylmethoxycarbonyl-5-oxotetrahydrofuran-3-carboxylic Acid

HRID 263681Notes

Reaction equation

HRID 263681 reaction equation
[O:1]=[C:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH:4]([C:10]([OH:12])=[O:11])[CH2:3]1.[C:13]1([C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N+]=[N-])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CC(C)=O>[C:13]1([CH:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:8][C:7]([CH:5]2[CH:4]([C:10]([OH:12])=[O:11])[CH2:3][C:2](=[O:1])[O:6]2)=[O:9])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 98259Tetrahydro-5-oxofuran-2,3-dicarboxylic acid

Product 1

HCID 18705268(2RS,3SR)-2-diphenylmethoxycarbonyl-5-oxotetrahydrofuran-3-carboxylic AcidYield 102.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

262 mg of (2RS,3SR)-5-oxotetrahydrofuran-2,3-dicarboxylic acid was dissolved in 5 ml of acetone, and 91 mg of diphenyldiazomethane was added thereto, followed by stirring at room temperature for 20 minutes. The reaction solution was evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1→10/1) to obtain 163 mg of the above-identified compound as white powder.

Workup

  1. customThe reaction solution was evaporated to dryness under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1→10/1)

Sources & evidence

ORD record
ord-d3523c644e1a4fe9adc49a880e321cd1
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Reaction notes

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