Benzyl Chloride → HCID 59533569, compound

HRID 1911865Notes

Reaction equation

HRID 1911865 reaction equation
Cl.[CH3:2][O:3][C@:4]1([CH3:19])[C@:15]([O:17][CH3:18])([CH3:16])[O:14][C@@H:7]2[CH2:8][NH:9][CH2:10][C@H:11]([CH2:12][OH:13])[C@H:6]2[O:5]1.C([O-])([O-])=O.[K+].[K+].[CH2:26](Cl)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C=O)C>[CH2:26]([N:9]1[CH2:10][C@H:11]([CH2:12][OH:13])[C@H:6]2[O:5][C@@:4]([O:3][CH3:2])([CH3:19])[C@:15]([O:17][CH3:18])([CH3:16])[O:14][C@@H:7]2[CH2:8]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 67109236HCID 67109236, compound

Product 1

HCID 59533569HCID 59533569, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2 (14.85 g, 50.0 mmol) in DMF (200 mL) was added K2CO3 (17.25 g, 125 mmol) and the mixture was stirred at 40° C. for about 4 hrs. At this point, BnCl (5.7 mL, 50.0 mmol) was added in one portion and the reaction was stirred at 40° C. overnight. The solvent was evaporated in vacuo and the residue was suspended in water (600 mL) and HCl was added to dissolve the residue. The solution was washed with Et2O and then basified with Na2CO3. The solution was extracted with EtOAc (2×) and the combined extracts were washed with water and then brine and then dried over MgSO4. The solution was filtered and the filtrate evaporated in vacuo to give the title compound (17.2 g, >95%) as a colorless to very pale yellow viscous oil which was used without further purification. 1H NMR (CDCl3) 7.3 (m, 5H), 3.6-3.8 (m, 2H), 3.5 (s, 3H), 3.4 (t, 1H), 3.26 (s, 3H), 3.268 (s, 3H), 2.9 (m, 2H), 2.2 (br s, 1H), 2.05 (m, 1H), 1.85 (t, 1H), 1.28 (s, 3H), 1.26 (s, 3H).

Workup

  1. stirringthe reaction was stirred at 40° C. overnight
  2. customThe solvent was evaporated in vacuo
  3. additionHCl was added
  4. dissolutionto dissolve the residue
  5. washThe solution was washed with Et2O
  6. extractionThe solution was extracted with EtOAc (2×)
  7. washthe combined extracts were washed with water
  8. dry with materialbrine and then dried over MgSO4
  9. filtrationThe solution was filtered
  10. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-2a23aa9b8b824b499f3a2bfcdc729a63
Source dataset
uspto-grants-2013_12
Patent number
US08604206B2

Reaction notes

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