Water → HCID 86585674, compound

HRID 2099337Notes

Reaction equation

HRID 2099337 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH3:12])[C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C@@:19]12(O)[N:26](C)[C@@H:23]([CH2:24][CH2:25]1)[CH2:22][CH:21]=[CH:20]2.[Na].O>C(#N)C>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH3:12])[C:8]([O:10][C@@:11]23[N:26]([CH3:19])[C@@H:23]([CH2:24][CH2:25]2)[CH2:22][CH:21]=[CH:20]3)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5360545Sodium2×HCID 15259765Methyl 2,2-diphenylpropionateHCID 53629842Tropenol

Product 1

HCID 86585674HCID 86585674, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.80 g (0.02 mol) of methyl 2,2-diphenylpropionate 3b, 2.78 g (0.02 mol) of tropenol, and 0.046 g of sodium are heated as a melt at 75 mbar for 4 hours over a bath of boiling water, shaking from time to time. After cooling, the sodium residues are dissolved with acetonitrile, the solution is evaporated to dryness, and the residue extracted with dichloromethane/water. The organic phase is washed with water, dried over MgSO4, and evaporated to dryness. From the residue, 4c is precipitated as the hydrochloride and this is recrystallized from acetone. Yield: 5.13 g (67% of theory); TLC: Rf value: 0.28 (eluent: sec-butanol/formic acid/water 75:15:10); melting point: 134° C.-135° C.

Workup

  1. temperatureAfter cooling
  2. customthe solution is evaporated to dryness
  3. extractionthe residue extracted with dichloromethane/water
  4. washThe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customFrom the residue, 4c is precipitated as the hydrochloride
  8. customthis is recrystallized from acetone

Sources & evidence

ORD record
ord-2d1195cc662144cfaf2c5ca9bfea2ae8
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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