Lithium hydroxide, monohydrate → HCID 11206816, compound

HRID 1716816Notes

Reaction equation

HRID 1716816 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=2)([CH3:11])[C:8](=[O:10])[CH:9]=1)=[O:4].O[Li].O>C1COCC1.CO>[C:12]1([C:7]2([CH3:11])[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][C:8]2=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11310903HCID 11310903, compound

Product 1

HCID 11206816HCID 11206816, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-cyclohex-1-enyl-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid methyl ester (47 mg, 0.2 mmol) in THF/MeOH (1/1, 2 mL) was added LiOH.H2O (8.4 mg, 0.2 mmol). The reaction mixture was stirred at room temperature for 5 hours. After concentration, the residue was dissolved in H2O (4 mL), washed with ethyl ether (2×5 mL). The separated aqueous layer was acidified to pH 2. This acidified solution was extracted with ethyl ether (3×5 mL). The extracts were dried (Na2SO4), filtered and concentrated. The crude product was purified with a silica gel column using EtOAc/AcOH (20/1) providing 35 mg (79%) of racemic 5-cyclohex-1-enyl-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid: LC-MS m/z 221 (M−1); 1H NMR (400 MHz, CDCl3) δ 6.30 (s, 1H), 5.90 (m, 1H), 2.16-2.06 (m, 3H), 1.79-1.70 (m, 1H), 1.67-1.51 (m, 4H), 1.58 (s, 3H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in H2O (4 mL)
  3. washwashed with ethyl ether (2×5 mL)
  4. extractionThis acidified solution was extracted with ethyl ether (3×5 mL)
  5. dry with materialThe extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified with a silica gel column

Sources & evidence

ORD record
ord-64f997fbdd3c4957941079799a8d84ea
Source dataset
uspto-grants-2010_09
Patent number
US07803837B2

Reaction notes

Loading…