Oxalic Acid → 2-(Trimethylsilyl)ethyl 2-(2-iodophenyl)butanoate

HRID 865473Notes

Reaction equation

HRID 865473 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:12][CH3:13])[C:9]([OH:11])=[O:10].N1C=CC=CC=1.[CH3:20][Si:21]([CH3:26])([CH3:25])[CH2:22][CH2:23]O.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C(O)=O>CC#N.CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:12][CH3:13])[C:9]([O:11][CH2:23][CH2:22][Si:21]([CH3:26])([CH3:25])[CH3:20])=[O:10]

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 224564332-(2-Iodophenyl)butanoic acid

Product 1

HCID 539675962-(Trimethylsilyl)ethyl 2-(2-iodophenyl)butanoateYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of the acid of Step 1 (103 g, 0.356 mol), pyridine (58 mL, 0.717 mol) and 2-(trimethylsilyl)ethanol (61.2 mL, 0.427 mol) in CH3CN (270 mL) was added a solution of dicyclohexylcarbodiimide (73.4 g, 0.356 mol) in CH3CN (100 mL). The reaction mixture was stirred at r.t. for 2 h, at which point 5M oxalic acid in DMF solution (11 mL) was added. After stirring for 30 min, the suspension was filtered and the filtrate was diluted with EtOAc, washed with water and dried over MgSO4. The crude product was distilled under reduced pressure to give 109 g of the title compound as a colorless oil (bp 120°-140° C./0.4 mm Hg).

Workup

  1. additionwas added
  2. filtrationthe suspension was filtered
  3. additionthe filtrate was diluted with EtOAc
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-94039dd6958444f1a8cbfcea078d9d5d
Source dataset
uspto-grants-1996_10
Patent number
US05565473

Reaction notes

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