Diisopropylamine → HCID 15789033, compound

HRID 2399669Notes

Reaction equation

HRID 2399669 reaction equation
C1([Li])C=CC=CC=1.C(NC(C)C)(C)C.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C(OCC)C>[Si:22]([CH2:21][C:17]1[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 79703-MethylpyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178506676HCID 178506676, compound

Product 1

HCID 15789033HCID 15789033, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a 500 ml 3 neck round bottomed flask stirring under N2 was charged 33.1 ml of 2M phenyl lithium, in 70/30 cyclohexane diethyl ether, (0.0662 moles, 1.0 eq.), to which 6.70 g of diisopropylamine (1.0 eq. 0.0662 moles) in 10 ml of diethylether was pipetted into the flask followed by rapid addition of 6.16 g of 3-picoline (1.0 eq., 0.066 moles) in 10 ml of diethylether and 10.0 g of tert-butyldimethylsilylchloride (1.0 eq., 0.0662 moles) in 10 ml diethyl ether. The temperature of the reaction was maintained below 35° C. with an ice bath during the additions. After 1 hour of stirring GLC indicated the reaction was complete. The reaction was quenched by adding 100 ml of water, extracted with 250 ml of diethylether and washed with 2×100 ml of water. The ether was dried over magnesium sulfate and concentrated to give 12.3 g of an orange oil. GLC indicated the crude mixture was 96% product. A 7.0 g portion was purified by flash chromatography with 1:4 ethyl acetate/hexane and afforded 3.8 g (48.7% yield based on chromatographic portion) of 3-(tert-butyldimethylsilyl)pyridine.

Workup

  1. temperatureThe temperature of the reaction was maintained below 35° C. with an ice bath during the additions
  2. customThe reaction was quenched
  3. additionby adding 100 ml of water
  4. extractionextracted with 250 ml of diethylether
  5. washwashed with 2×100 ml of water
  6. dry with materialThe ether was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7b36a669f20f48a7897a455742dd06e0
Source dataset
uspto-grants-1995_09
Patent number
US05451563

Reaction notes

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