Water → HCID 10014874, compound

HRID 488156Notes

Reaction equation

HRID 488156 reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4]Br.[N-:17]=[N+:18]=[N-:19].[Na+].O>CN(C=O)C>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3]\[CH2:4][N:17]=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 5366048(2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene

Product 1

HCID 10014874HCID 10014874, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl bromide (1.5 g, 5.26 mmol) and sodium azide (0.68 g, 10.5 mmol) in DMF (20 mL) was stirred at room temperature for 0.5 hours, then poured into cold water and extracted with ether. The ethereal extract was washed with brine, dried, filtered and evaporated to yield a residue. Purification of the residue by flash chromatography on a silica gel column, using hexane as the eluant, afforded the title compound as an oil (1.2 g, 4.85 mmol, 92%) NMR (CDCl3): δ5.35 (H, t, J=7Hz), 5.10 (2H, m), 3.78 (2H, d, J=7Hz), 1.9-2.2 (8H, m), 1.72 (3H, s), 1.68 (3H, s) 1.60 (6H, s).

Workup

  1. extractionextracted with ether
  2. extractionThe ethereal extract
  3. washwas washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a residue
  8. customPurification of the residue by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-7a26416c469e42c98d4859eba10588b6
Source dataset
uspto-grants-1994_03
Patent number
US05298655

Reaction notes

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