Methanol → HCID 66733598, compound

HRID 1472490Notes

Reaction equation

HRID 1472490 reaction equation
[S:1]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@H:2]1[O:10][C@@H:9]([CH3:11])[C@@H:7]([OH:8])[C@@H:5]([OH:6])[C@@H:3]1[OH:4].[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1.[OH-].[Na+].CO>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][O:4][C@H:3]2[C@H:5]([O:6][CH2:18][C:19]3[CH:26]=[CH:25][C:22]([CH3:23])=[CH:21][CH:20]=3)[C@H:7]([O:8][CH2:18][C:19]3[CH:26]=[CH:25][C:22]([CH3:23])=[CH:21][CH:20]=3)[C@H:9]([CH3:11])[O:10][C@@H:2]2[S:1][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 77224-Methylbenzyl chlorideHCID 14798Sodium HydroxideHCID 54499710HCID 54499710, compound

Product 1

HCID 66733598HCID 66733598, compoundYield 29.5%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3.0 g (11.9 mmol) of compound of example 9 and 1.22 g (3.6 mmol, 0.3 eq.) tetrabutylammonium hydrogen sulphate is suspended in 20 ml of dichloromethane. The suspension is refluxed, under vigorous stirring, until a homogenous solution is obtained. To this solution p-methylbenzyl chloride (7.23 ml, 53.6 mmol, 4.5 eq) followed by 5 ml of 50% (w/w) NaOH solution are added. The thick emulsion is refluxed for 3 hours while vigorously stirred, then 8 ml of MeOH are added and the reaction mixture is additionally refluxed for one night. After cooling DCM and water are added. The phases are separated and the aqueous phase is washed with DCM. The combined organic phases are washed with brine and the solvents are evaporated. The crude product is purified by column chromatography. The purest fractions are collected and the product is recrystallized from MeOH to yield 2.0 g of white solid. M.p.: 84-85° C.

Workup

  1. temperatureThe suspension is refluxed, under vigorous stirring, until a homogenous solution
  2. customis obtained
  3. additionare added
  4. temperatureThe thick emulsion is refluxed for 3 hours
  5. temperaturethe reaction mixture is additionally refluxed for one night
  6. additionare added
  7. customThe phases are separated
  8. washthe aqueous phase is washed with DCM
  9. washThe combined organic phases are washed with brine
  10. customthe solvents are evaporated
  11. customThe crude product is purified by column chromatography
  12. customThe purest fractions are collected
  13. customthe product is recrystallized from MeOH

Sources & evidence

ORD record
ord-65a8df165b744d58881a760de16a1f13
Source dataset
uspto-grants-2015_04
Patent number
US09012625B2

Reaction notes

Loading…