Methyl 2-phenyl-2-propylpentanoate → HCID 11586590, compound

HRID 494436

Reaction equation

HRID 494436 reaction equation
[C:1]1([C:7]([CH2:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:8]([O:10]C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1>[C:1]1([C:7]([CH2:15][CH2:16][CH3:17])([CH2:12][CH2:13][CH3:14])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 11658708Methyl 2-phenyl-2-propylpentanoate

Product 1

HCID 11586590HCID 11586590, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 1B (7.63 g, 32.61 mmol) and potassium trimethylsilanoate (23.2 g of 90% material, 163 mmol) in tetrahydrofuran (163 mL) was warmed at reflux for 18 hours. The solution was cooled to 25° C. and concentrated in vacuo to remove the tetrahydrofuran. A solution of the residue in water (250 mL) was cooled to 0° C., and adjusted to pH 1 by addition of 4 N HCl solution. The resulting precipitate was collected by filtration, washed with water and dried to give the title compound (6.78 g, 95%). 1H NMR (300 MHz, CDCl3): δ 7.25 (m, 5 H), 1.99 (m, 4 H), 1.12 (m, 4 H), 0.90 (t, J=7.17 Hz, 6 H).

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated in vacuo
  3. customto remove the tetrahydrofuran
  4. temperatureA solution of the residue in water (250 mL) was cooled to 0° C.
  5. additionadjusted to pH 1 by addition of 4 N HCl solution
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-8277ce1f669944fb9703e53b428dc2b6
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Linked notes

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