HCID 15415311, compound → HCID 68670470, compound

HRID 2071125Notes

Reaction equation

HRID 2071125 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:2].[CH3:19][Mg+].[Br-]>CCOCC>[OH:2][CH:1]([C:3]1[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[C:5]([CH:4]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:19]

Participants

4

Reactant 2

HCID 15415311HCID 15415311, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 68670470HCID 68670470, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of diethyl 5-formylisophthalate (2.83 g, 11.3 mmol) in ether (20 mL) was added MeMgBr (3.8 ml of 3.0 M solution, 11.3 mmol) dropwise. The resulting yellow suspension was stirred for 5 h and quenched with saturated aqueous NH4Cl. The resulting mixture was extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (20% EtOAc in hexanes) to provide diethyl 5-(1-hydroxyethyl)isophthalate (1.15 g, 40%) as a white solid. 1H NMR (CDCl3): d 8.60-8.61 (m, 1H), 8.26-8.27 (m, 2H), 5.02-5.09 (m, 1H), 4.45 (q, J=7.2 Hz, 2H), 1.56 (d, J=6.3 Hz, 3H), 1.45 (t, J=7.2, 3H).

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-08eeb01727174321a3d6c817ff5c6414
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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