Methanol → HCID 67486946, compound

HRID 2103620Notes

Reaction equation

HRID 2103620 reaction equation
C([O:3][C:4](=[O:19])/[C:5](/[C:13]1S[C:15]([Br:18])=[CH:16][CH:17]=1)=[CH:6]/[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[Na+].[CH3:22]O>O1CCOCC1>[Br:18][C:15]1[CH2:22][C:13](/[C:5](=[CH:6]/[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)/[C:4]([OH:3])=[O:19])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67484367HCID 67484367, compound

Product 1

HCID 67486946HCID 67486946, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dissolve (Z)-2-(5-bromo-thiophen-2-yl)-3-cyclohexyl-acrylic acid ethyl ester (116 g, 0.338 mol) in MeOH (600 mL) and dioxane (600 mL), add sodium hydroxide (730 mL, 1.0 M, 0.730 mol) and stir 16 h at ambient temperature. Concentrate the reaction mixture, acidify the aqueous residue with concentrated hydrochloric acid (75 mL) and extract with ethylacetate. Wash with saturated sodium chloride, dry over sodium sulfate and remove solvent under vacuum to get 124 g crude product. MS (m/e): 315.0/317.0 (M+H).

Workup

  1. concentrationConcentrate the reaction mixture
  2. extractionextract with ethylacetate
  3. washWash with saturated sodium chloride
  4. dry with materialdry over sodium sulfate
  5. customremove solvent under vacuum

Sources & evidence

ORD record
ord-f0882d57b6394e96bd39e5c1c12036b0
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

Loading…