Lithium hydroxide, monohydrate → HCID 71303406, compound

HRID 2176225Notes

Reaction equation

HRID 2176225 reaction equation
C([O:3][C:4]([C:6]1([CH:13]=[CH2:14])[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+]>O1CCOCC1.O>[O:12]=[C:9]1[CH2:8][CH2:7][C:6]([CH:13]=[CH2:14])([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71304285HCID 71304285, compound

Product 1

HCID 71303406HCID 71303406, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of the commercially available 4-oxo-1-vinyl-cyclohexanecarboxylic acid ethyl ester (provided by Small Molecules Inc.), (1.20 g, 6.11 mmol) in 1,4-dioxane (20 mL) was treated with a solution of lithium hydroxide monohydrate (734 mg, 30.6 mmol) in water (10 mL). After stirring at 50° C. for 2 h, the volatiles were removed in vacuo. The residue was partitioned between water and diethyl ether. The aqueous layer was acidified to pH 1 by addition of saturated potassium hydrogen sulfate solution and was extracted with ethyl acetate (3×). The organic layer was dried over anhydrous magnesium sulfate, filtered and the volatiles were removed in vacuo to afford the title compound (1.00 g, 97%) as a clear gum. 1H NMR (300 MHz, CDCl3) δ 1.92-2.08 (m, 2H), 2.36-2.59 (m, 6H), 5.34 (d, J=17.5 Hz, 1H), 5.35 (d, J=10.5 Hz, 1H), 5.97 (dd, J=17.5, 10.5 Hz, 1H), 11.30 (br s, 1H).

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe residue was partitioned between water and diethyl ether
  3. additionThe aqueous layer was acidified to pH 1 by addition of saturated potassium hydrogen sulfate solution
  4. extractionwas extracted with ethyl acetate (3×)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-b33f889cc7f047f987f9851b6841cba0
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

Loading…