Dimethylformamide → HCID 13146586, compound

HRID 1701935Notes

Reaction equation

HRID 1701935 reaction equation
[H-].[Na+].CN(C)[CH:5]=[O:6].[CH3:8][Si:9]([CH3:23])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:10]1[CH:11]=[C:12](O)[CH:13]=[CH:14][CH:15]=1.S(OC)(OC)(=O)=O>O>[CH3:8][Si:9]([CH3:23])([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:10]1[CH:11]=[C:12]([O:6][CH3:5])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 13146585HCID 13146585, compound

Product 1

HCID 13146586HCID 13146586, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a 0° C. slurry of 3.98 g. (0.166 mole) of sodium hydride in 50 ml. dimethylformamide was slowly added a solution of 26.1 g. (0.111 mole) of 3-(dimethyl-n-hexylsilyl)phenol in 50 ml. dimethylformamide. Following addition, the reaction mixture was stirred 1 hr at 25° C. and cooled to 0° C. To the cooled reaction mixture, 20.9 g. (0.166 mole) of dimethyl sulfate was slowly added. Following addition, the reaction was stirred for 2 hr at 25° C. and then added to 200 ml. water. The quenched reaction mixture was extracted with three 100 ml. portions of hexane. The hexane extract was dried over anhydrous magnesium sulfate and evaporated to an oil. This oil was purified by column chromatography on 500 g. of silica gel eluted with 1% diethyl ether hexane to yield 14.8 g. (53%) of the title compound as an oil.

Workup

  1. customTo a 0° C.
  2. additionaddition
  3. temperaturecooled to 0° C
  4. customTo the cooled reaction mixture, 20.9 g
  5. additionaddition
  6. stirringthe reaction was stirred for 2 hr at 25° C.
  7. additionadded to 200 ml
  8. customThe quenched reaction mixture
  9. extractionwas extracted with three 100 ml
  10. extractionThe hexane extract
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. customevaporated to an oil
  13. customThis oil was purified by column chromatography on 500 g
  14. washof silica gel eluted with 1% diethyl ether hexane
  15. customto yield 14.8 g

Sources & evidence

ORD record
ord-f3948036fe07415e8cd0b45715be9886
Source dataset
uspto-grants-1983_04
Patent number
US04379783

Reaction notes

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