Lithium hydroxide, monohydrate → HCID 58611848, compound

HRID 2375227Notes

Reaction equation

HRID 2375227 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].O>O1CCCC1.O>[C:1]([O:5][C:6]([C:8]1([C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58611836HCID 58611836, compound

Product 1

HCID 58611848HCID 58611848, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[1-(tert-butoxycarbonyl)cyclohexyl]benzoate (1) (0.273 g, 0.86 mmol) in tetrahydrofuran (5 ml) was added 0.63 N LiOH water solution (3 ml, 1.89 mmol) and the resultant suspension was stirred at ambient temperature for 5 days. The reaction mixture was diluted with water (20 ml) and saturated NaH2PO4 (5 ml), and the obtained suspension was extracted with ethyl acetate (2×30 ml). The extract was washed with brine (15 ml), dried (Na2SO4), and the solvent was removed in vacuo. The residue was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (8:2:01) as eluent to give the title compound (0.231 g, 88%) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.07-1.91 (8H, m); 1.35 (9H, s); 2.20-2.63 (2H, m); 7.52 (2H, d, J=8.5 Hz); 8.06 (2H, d, J=8.5 Hz); 11.20 (1H, br s).

Workup

  1. extractionthe obtained suspension was extracted with ethyl acetate (2×30 ml)
  2. washThe extract was washed with brine (15 ml)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica gel with toluene-ethyl acetate-acetic acid (8:2:01) as eluent

Sources & evidence

ORD record
ord-e6b50b13fb9140aa9af3e125ce640d3f
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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