Triethylamine → HCID 131715647, compound

HRID 845892Notes

Reaction equation

HRID 845892 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1([CH3:34])[CH2:18][C:17](=[O:19])[C:16]([CH3:21])([CH3:20])[C:15]2[CH:14]=[C:13](/[C:22](/C)=[CH:23]/[C:24]3[CH:32]=[CH:31][C:27](C(O)=O)=[CH:26][CH:25]=3)[CH:12]=[CH:11][C:10]1=2.ClC([O:38][CH2:39][CH3:40])=O.[N-:41]=[N+:42]=[N-:43].[Na+]>CC(C)=O.O>[CH3:8][C:9]1([CH3:34])[CH2:18][C:17](=[O:19])[C:16]([CH3:21])([CH3:20])[C:15]2[CH:14]=[C:13]([CH2:22][CH:23]=[CH:24][C:25]3[CH:26]=[CH:27][CH:31]=[CH:32][C:40]=3[C:39]([N:41]=[N+:42]=[N-:43])=[O:38])[CH:12]=[CH:11][C:10]1=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 13604817HCID 13604817, compound

Product 1

HCID 131715647HCID 131715647, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 6 ml of triethylamine in 30 ml of acetone is allowed to run into a suspension of 12.7 g (35 mmol) of (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-7-oxo-naphth-2-yl)-1-propenyl]-benzoic acid (Example 2) in 60 ml of acetone and 20 ml of water, at 0°-5° C. At 0° C. 4.5 ml (5.2 g, 55 mmol) of ethyl chloroformate are added dropwise, the solution is stirred for a further 10 minutes and a solution of 3.5 g (55 mmol) of sodium azide in 7.5 ml of water is then added dropwise. The solution is stirred at 0° C. for a further 2 hours, the finely crystalline solid is filtered off under suction and the residue is washed with a little water and ethanol and dried, to give 10.8 g of the title compound which is processed further without purification (see Example 11).

Workup

  1. customAt 0° C
  2. stirringThe solution is stirred at 0° C. for a further 2 hours
  3. filtrationthe finely crystalline solid is filtered off under suction
  4. washthe residue is washed with a little water and ethanol
  5. customdried

Sources & evidence

ORD record
ord-ea31aff6d2d84ef2b6f1866160f49747
Source dataset
uspto-grants-1988_07
Patent number
US04760174

Reaction notes

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