Hydrochloric Acid → HCID 19926462, compound

HRID 1647168Notes

Reaction equation

HRID 1647168 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][CH2:11][CH2:12][O:13]C.C[Si](I)(C)C.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 19926464HCID 19926464, compound

Product 1

HCID 19926462HCID 19926462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-3-(3-methoxy-1-propoxy)-2-methylpyridine (120 mg, 0.56 mmol) in 2 ml of CDCl3 was added trimethylsilyl iodide (0.16 ml, 1.3 mmol), this was done in a NMR tube. The reaction was complete after four days as indicated by the absence of a signal for the OCH3 protons at 3.3 ppm in the NMR spectrum. The solution was poured over 10 ml of 1M HCl whereupon the mixture was stirred for 5 minutes with 10 ml of methylene chloride. The aqueous layer was separated, treated with K2CO3 until pH=10 and extracted with methylene chloride. The organic phase was dried over Na2SO4 and evaporated. This afforded 0.049 g (43%) of the desired product as a yellow oily film.

Workup

  1. customThe aqueous layer was separated
  2. additiontreated with K2CO3 until pH=10
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-840fe5f0a8134f6dac6276dbbe4fc090
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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