tert-Butyl methyl ether → HCID 19867317, compound

HRID 1198836Notes

Reaction equation

HRID 1198836 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH:17]=O)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:19]OC(C)(C)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH:17]=[CH2:19])=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl ether2×HCID 19867190HCID 19867190, compound

Product 1

HCID 19867317HCID 19867317, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

A suspension of 6.64 g of methyltriphenylphosphonium bromide in 80 ml of t-butyl methyl ether in a sulphonation flask fitted with a mechanical stirrer is treated while gassing with argon at -10° C. within 3 minutes with 2.12 g of solid potassium t-butylate. The mixture is stirred at room temperature for a further 1 hour, then treated at 0° C. within 5 minutes with a solution of 3.61 g of 4-[2-(p-bromophenyl)- -5-pyridyl]butyraldehyde in 20 ml of t-butyl methyl ether and stirred at room temperature for a further 15 hours. The reaction mixture is subsequently partitioned three times in diethyl ether/water. The organic extracts are washed twice with water, dried over magnesium sulphate, filtered and evaporated. The residue is taken up in ethyl acetate and then the mixture is diluted with petroleum ether and filtered. Evaporation of the filtrate and purification of the residue by chromatography on silica gel gives 2-(p-bromophenyl)-5-(4-pentenyl)pyridine.

Workup

  1. customfitted with a mechanical stirrer
  2. additionis treated
  3. stirringstirred at room temperature for a further 15 hours
  4. customThe reaction mixture is subsequently partitioned three times in diethyl ether/water
  5. washThe organic extracts are washed twice with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. additionthe mixture is diluted with petroleum ether
  10. filtrationfiltered
  11. customEvaporation of the filtrate and purification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-0e9cc74741974da9ad1de185d66c510b
Source dataset
uspto-grants-1990_02
Patent number
US04898455

Reaction notes

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