Triethylamine → HCID 58883445, compound

HRID 1765911Notes

Reaction equation

HRID 1765911 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:17]([OH:19])=O)[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]2([CH3:16])[CH3:15])#[CH:2].C(N(CC)CC)C.ClC(OCC)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:17]([N:33]=[N+:34]=[N-:35])=[O:19])[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]2([CH3:16])[CH3:15])#[CH:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 12137002HCID 12137002, compound2×

Product 1

HCID 58883445HCID 58883445, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred, cooled (ice bath) solution of 8-ethynyl-2,2,4,4-tetramethyl-chroman-6-carboxylic acid (Intermediate 210, 0.52 g, 2 mmol) in anhydrous tetrahydrofuran (10 mL) under argon, was treated with triethyl amine (0.86 mL, 6 mmol) follwed by ethyl chloroformate (0.25 mL, 2.6 mmol) and the resulting reaction mixture was allowed to warm to ambient temperature and stirred for 2 h. Sodium azide 0.19 g, 3 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was then diluted with water and extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated to a residue that was purified by flash column chromatography over silica gel (230–400 mesh) to afford the title compound as a yellow solid (0.32 g, 56%).

Workup

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture was stirred overnight
  3. extractionextracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a residue that
  8. customwas purified by flash column chromatography over silica gel (230–400 mesh)

Sources & evidence

ORD record
ord-eae6c4da1f9b45fe8b1863c36b1f5374
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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