Sodium hydride → HCID 66733688, compound

HRID 1472491Notes

Reaction equation

HRID 1472491 reaction equation
[H-].[Na+].Br[CH2:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13].[S:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:15]1[O:23][C@@H:22]([CH3:24])[C@@H:20]([OH:21])[C@@H:18]([OH:19])[C@@H:16]1[OH:17]>CN(C=O)C>[CH3:13][C:6]1[CH:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[C:5]=1[CH2:4][O:17][C@H:16]1[C@H:18]([O:19][CH2:4][C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH3:13])[C@H:20]([O:21][CH2:4][C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH3:13])[C@H:22]([CH3:24])[O:23][C@@H:15]1[S:14][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2334002-(bromomethyl)-1,3,5-trimethylbenzeneHCID 54499710HCID 54499710, compound

Product 1

HCID 66733688HCID 66733688, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A dry 250 ml flask is filled with 6.6 g (152 mmol) of sodium hydride in mineral oil emulsion (55%). Dry dimethylformamide (10 ml) is added and the mixture is cooled to 0° C. To this mixture bromomethylmesitylene (32.4 g, 152 mmol) in dry DMF (20 ml) is added. Compound of example 9 (10 g, 39 mmol) is dissolved in dry DMF (20 mL) and added very to the above mixture over 40 minutes. After an additional hour the ice-bath is removed and the reaction is stirred at room temperature for 21 hours. Methanol (15 ml) is added to quench and the reaction mixture is stirred for another hour, then it is diluted with ethyl acetate (200 ml) and extracted with sat. NaHCO3 (200 ml), 1N HCl (200 ml), water (200 ml) and brine (200 ml). The title compound is obtained after column chromatography purification and crystallization.

Workup

  1. additionadded very to the above mixture over 40 minutes
  2. customAfter an additional hour the ice-bath is removed
  3. additionMethanol (15 ml) is added
  4. customto quench
  5. stirringthe reaction mixture is stirred for another hour
  6. additionit is diluted with ethyl acetate (200 ml)
  7. extractionextracted with sat. NaHCO3 (200 ml), 1N HCl (200 ml), water (200 ml) and brine (200 ml)

Sources & evidence

ORD record
ord-328b4b543c93417bb337b22504511da6
Source dataset
uspto-grants-2015_04
Patent number
US09012625B2

Reaction notes

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