Sodium hydride → HCID 67102642, compound

HRID 1820942Notes

Reaction equation

HRID 1820942 reaction equation
[Br-].[PH4+].C1([C:9](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:10][O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH3:16])C=CC=CC=1.[H-].[Na+].[CH3:32][C:33]1[CH:48]=[CH:47][CH:46]=[C:45]([CH3:49])[C:34]=1[CH2:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH:40]=O>CS(C)=O>[CH2:10]([O:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH:16]=[CH:40][C:39]1[CH:42]=[CH:43][CH:44]=[C:37]([O:36][CH2:35][C:34]2[C:33]([CH3:32])=[CH:48][CH:47]=[CH:46][C:45]=2[CH3:49])[CH:38]=1)[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57892224HCID 57892224, compoundHCID 86608894HCID 86608894, compound

Product 1

HCID 67102642HCID 67102642, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
23.200000762939453 °C

Procedure

A mixture of 13.29 g of triphenylethylvalerate phosphonium bromide and 0.745 g of sodium hydride in 40 ml of DMSO was stirred for 30 min, under nitrogen in a 3-necked, 100 ml round bottom flask equipped with a stir bar, reflux condenser with a nitrogen inlet and a thermocouple. The mixture changed from light yellow to brown and heated to 40.2° C. from 23.2° C. 5.00 g of 3-(2,6-dimethylbenzyloxy)benzaldehyde was dissolved in 20 ml of DMSO and added, dropwise over a 4 min. period to the reaction mixture. The mixture heated to 26.8° C. from 21.8° C. The reaction mixture was stirred and allowed to cool to room temperature. The reaction was analyzed after 1 hr. and LC-MS showed almost all the starting aldehyde left and ˜3% desired product. The reaction mixture was heated to 50° C. and stirred for 3 hrs. The reaction was analyzed after 2 and 3 hrs. LC-MS showed ˜20% starting aldehyde left and 17% desired product. The reaction was cooled to room temperature and placed in a refrigerator overnight.

Workup

  1. customequipped with a stir bar
  2. temperaturereflux condenser with a nitrogen inlet
  3. additionadded, dropwise over a 4 min. period to the reaction mixture
  4. temperatureThe mixture heated to 26.8° C. from 21.8° C
  5. stirringThe reaction mixture was stirred
  6. temperatureto cool to room temperature
  7. waitThe reaction was analyzed after 1 hr
  8. waitleft

Sources & evidence

ORD record
ord-87a760048eab4184a9d2ea7d0402f150
Source dataset
uspto-grants-2009_10
Patent number
US07605181B2

Reaction notes

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