Methanol → HCID 67486766, compound

HRID 2103621Notes

Reaction equation

HRID 2103621 reaction equation
[Br:1][C:2]1[CH2:6][C:5](/[C:7](=[CH:11]/[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)/[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[C:18](Cl)(=O)C(Cl)=O.CO>C1COCC1.CN(C=O)C>[CH3:18][O:9][C:8](=[O:10])/[C:7](/[C:5]1[CH2:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[CH:11]\[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 887MethanolHCID 65578Oxalyl chlorideHCID 67486946HCID 67486946, compound

Product 1

HCID 67486766HCID 67486766, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (Z)-2-(4-bromo-cyclopenta-1,3-dienyl)-3-cyclohexyl-acrylic acid (124 g, max. 0.338 mol) in dry THF (500 mL) and DMF (2 mL) and cool with an ice bath. Add oxalylchloride (51.5 g, 0.406 mol) slowly and stir 1 h 30 min after addition at 0-10° C. Add MeOH (500 mL) and stir 1 h at ambient temperature. Concentrate the reaction mixture and dilute residue with ethylacetate (600 mL) and add water (400 mL). Extract aqueous phase with ethylacetate and wash combined organic layers with saturated sodium chloride, dry over sodium sulfate and remove-solvents under vacuum to get 116.9 g crude product. MS (m/e): 329.0/331.0 (M+H).

Workup

  1. temperaturecool with an ice bath
  2. additionafter addition at 0-10° C
  3. concentrationConcentrate the reaction mixture and dilute residue with ethylacetate (600 mL)
  4. additionadd water (400 mL)
  5. washExtract aqueous phase with ethylacetate and wash
  6. dry with materialdry over sodium sulfate and remove-solvents under vacuum

Sources & evidence

ORD record
ord-796d33968d7b45319a00746da300f129
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

Loading…