Isopropanol → HCID 54496590, compound

HRID 580978Notes

Reaction equation

HRID 580978 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[CH3:12][CH:13](O)[CH3:14].Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH:13]([CH3:14])[CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27800902-Iodophenylacetic acid

Product 1

HCID 54496590HCID 54496590, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-iodophenyl)acetic acid (0.50 g) and propan-2-ol (0.142 ml) in dry dimethylformamide (10 ml) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.458 g) with stirring at ambient temperature under an atmosphere of argon. After 18 hours the reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (3×50 ml) and brine. The aqueous layers were back-extracted with ethyl acetate (50 ml) and the organic layers were combined, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (Varian Band Elut S1 silica gel) eluting with dichloromethane to give 2-propyl 2-(2-iodophenyl)acetate (232 mg) as a yellow oil, NMR: 1.2(6H, d), 3.8(2H, s), 4.9(1H, m), 7.0(1H, m), 7.4(2H, d) and 7.85(1H, d).

Workup

  1. washwashed with water (3×50 ml) and brine
  2. extractionThe aqueous layers were back-extracted with ethyl acetate (50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel (Varian Band Elut S1 silica gel)
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-58e64464ed7d4c34aa3ae8878051a45d
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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