Sodium Hydroxide → 2-(5-Chloropentyl)pyridine

HRID 2232722Notes

Reaction equation

HRID 2232722 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]O.[OH-].[Na+]>ClCCl>[Cl:3][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 143474782-Pyridinepentanol

Product 1

HCID 147508302-(5-Chloropentyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of 4.1 mL of thionyl chloride in 30 mL of dichloromethane was added over 10 minutes to a stirred solution of 6.65 g of 2-pyridinepentanol in 60 mL of dichloromethane maintained at -5° C. After the addition was complete, the mixture was stirred at room temperature for 17 hours, then was rechilled to 5° C. as 150 ml of 1N NaOH was added dropwise over 10 minutes. The layers were separated and the aqueous layer was extracted with 75 mL of dichloromethane. The organic layers were washed with brine, then were combined, dried (K2CO3) and evaporated to yield 7.4 g of 2-(5-chloropentyl)pyridine as an oil.

Workup

  1. additionAfter the addition
  2. additionwas added dropwise over 10 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 75 mL of dichloromethane
  5. washThe organic layers were washed with brine
  6. dry with materialdried (K2CO3)
  7. customevaporated

Sources & evidence

ORD record
ord-b1682c3b1b2640589a11de8c5f4c0dd2
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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