Methanol → HCID 90018946, compound

HRID 571133Notes

Reaction equation

HRID 571133 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10](/[CH:13]=[C:14](/[C:17]([O:19]C)=[O:18])\[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[S:9][C:10](/[CH:13]=[C:14](\[CH2:15][CH3:16])/[C:17]([OH:19])=[O:18])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 117992948HCID 117992948, compound

Product 1

HCID 90018946HCID 90018946, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[(1E)-2-(methoxycarbonyl)-but-1-en-1-yl]thiophene-2-carboxylic acid tert-butyl ester (34.6 g, 120 mol) was dissolved in tetrahydrofuran (150 mL), and methanol (60 mL), 1 N lithium hydroxide solution (144 mL, 144 mmol) was added, and the mixture was stirred at room temperature for 2 days. The mixture was concentrated under reduced pressure. 0.5 N-Hydrochloric acid solution and ethyl acetate were added to the obtained residue, the organic layer was extracted, and the aqueous layer was extracted three times with ethyl acetate. The organic layers were collected, washed with brine, and dried over anhydrous magnesium sulfate. After filtration, the solvent of the filtrate was evaporated under reduced pressure to give the title compound (32.2 g, 114 mmol, 95%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. addition0.5 N-Hydrochloric acid solution and ethyl acetate were added to the obtained residue
  3. extractionthe organic layer was extracted
  4. extractionthe aqueous layer was extracted three times with ethyl acetate
  5. customThe organic layers were collected
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. customthe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fd593653aba243e09fb873bc28cb1802
Source dataset
uspto-grants-2015_05
Patent number
US09024044B2

Reaction notes

Loading…