Dimethylformamide → HCID 19966113, compound

HRID 1734895Notes

Reaction equation

HRID 1734895 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C)C=O.[CH:21]1([CH2:27][CH:28]([OH:43])[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:39]([CH3:42])([CH3:41])[CH3:40])=[C:34]([N+:36]([O-:38])=[O:37])[CH:35]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C1C=CN=CC=1)C.O>[CH:21]1([CH2:27][CH:28]([O:43][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:39]([CH3:41])([CH3:40])[CH3:42])=[C:34]([N+:36]([O-:38])=[O:37])[CH:35]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 19966070HCID 19966070, compound

Product 1

HCID 19966113HCID 19966113, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

973 mg (6.46 mmol) of t-butyldimethylsilyl chloride, 0.90 ml (6.46 mmol) of triethylamine and 67 mg (0.55 mmol) of 4-(N,N-dimethylamino)pyridine were added to 10 ml of a dimethylformamide solution containing 1.74 g of 5-(3-cyclohexyl-2-hydroxypropyl)-2-t-butyl-1-nitrobenzene [prepared as described in step (i) above]. The mixture was then stirred for 1 hour and 20 minutes at room temperature, and then for 2.5 hours at 40° C. At the end of this time, the reaction solution was poured in water and extracted with a 3:1 by volume mixture of hexane and ethyl acetate. The organic layer was washed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride, in that order. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 75 g of silica gel. Elution with a 1:9 by volume mixture of diethyl ether and hexane afforded 2.22 g (yield 96% over the 2 steps) of the title compound as an oily substance.

Workup

  1. waitfor 2.5 hours at 40° C
  2. extractionextracted with a 3:1 by volume mixture of hexane and ethyl acetate
  3. washThe organic layer was washed with dilute aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride, in that order
  4. customThe solvent was then removed by distillation under reduced pressure
  5. washElution with a 1:9
  6. additionby volume mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-f09b1404c0bd49ecb00b2b1535e63882
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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