Hydrochloric Acid → HCID 59729415, compound

HRID 1669295Notes

Reaction equation

HRID 1669295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:15][O:16]C)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][N:3]=1.Cl>O1CCCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:15]=[O:16])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 72369211HCID 72369211, compound

Product 1

HCID 59729415HCID 59729415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-5-(1-methoxymethylene-heptyl)-pyridine is dissolved into anhydrous tetrahydrofuran (20 mL) and concentrated hydrochloric acid (2 mL) are added with stirring under nitrogen. The reaction is heated to 50° C. and monitored by HPLC. Upon complete consumption of starting material, the reaction is carefully neutralized with sodium hydroxide, extracted with diethyl ether, washed, dried, and concentrated. The 2-(6-Chloro-pyridin-3-yl)-octanal (1.02 g, 4.26 mmol), 32% two steps, is obtained in purified form after flash column chromatography.

Workup

  1. additionare added
  2. customUpon complete consumption of starting material
  3. extractionextracted with diethyl ether
  4. washwashed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-86ed4aeaaddc4e25b9ece582e8bc5794
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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