Water → HCID 68874545, compound

HRID 494569Notes

Reaction equation

HRID 494569 reaction equation
[CH:1]1([CH2:7][C:8]([CH3:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11]C)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si](C)(C)[O-].[K+].O>O1CCCC1>[CH:1]1([CH2:7][C:8]([CH3:19])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 23668039Potassium trimethylsilanolateHCID 68874551Methyl 3-cyclohexyl-2-methyl-2-phenylpropanate

Product 1

HCID 68874545HCID 68874545, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 41A (4.02 g, 15.4 mmol) and potassium trimethyl silanolate (11.0 g, 77.2 mmol) in tetrahydrofuran (80 mL) was heated to reflux for 18 hours. The mixture was cooled to 25° C., treated with water (10 mL), and concentrated in vacuo to remove the tetrahydrofuran. The residue was dissolved in water and washed with hexane. The aqueous layer was acidified to pH 1 with 1N hydrochloric acid and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.80 g, 99%). 1H NMR (300 MHz, CDCl3): δ ppm 1.10 (m, 6H) 1.57 (m, 8H) 1.82 (m, 1H) 2.04 (m, 1H) 7.32 (m, 5H).

Workup

  1. temperatureto reflux for 18 hours
  2. concentrationconcentrated in vacuo
  3. customto remove the tetrahydrofuran
  4. dissolutionThe residue was dissolved in water
  5. washwashed with hexane
  6. extractionextracted three times with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b81473bf6b034090b9c3a0eef624f017
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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