Methanol → HCID 10875084, compound

HRID 1472489Notes

Reaction equation

HRID 1472489 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].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+].CO>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH2:18]([O:4][C@H:3]1[C@H:5]([O:6][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:7]([O:8][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:9]([CH3:11])[O:10][C@@H:2]1[S:1][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 54499710HCID 54499710, compound

Product 1

HCID 10875084HCID 10875084, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of compound of example 9 (50 g) and tetrabutylammonium hydrogen sulphate (19.9 g) in DCM is warmed until a homogenous solution is obtained. To this solution benzyl chloride (101 ml) followed by 250 ml of 50% (w/w) NaOH-solution are added. The thick emulsion is refluxed under vigorous stirring. After 1.5 h 12 ml of MeOH is added and the reaction mixture is additionally refluxed for overnight. After cooling it is diluted with 200 ml of DCM and washed with water (400 ml) and brine (100 ml). DCM is evaporated to give a yellow oil (˜150 g) to which 230 ml of MeOH is slowly added. The resulting suspension is stirred overnight at 4° C., the precipitate is filtered, washed with 200 ml of n-heptane and dried i.v. to yield 68 g of white powder. Physical characteristics are in good agreement with those reported [7].

Workup

  1. temperatureis warmed until a homogenous solution
  2. customis obtained
  3. additionare added
  4. temperatureThe thick emulsion is refluxed under vigorous stirring
  5. temperaturethe reaction mixture is additionally refluxed for overnight
  6. temperatureAfter cooling it
  7. washwashed with water (400 ml) and brine (100 ml)
  8. customDCM is evaporated

Sources & evidence

ORD record
ord-2ab5e69bc49f404d9801e1af3c64e289
Source dataset
uspto-grants-2015_04
Patent number
US09012625B2

Reaction notes

Loading…