Triethylamine → HCID 58883445, compound

HRID 1870047Notes

Reaction equation

HRID 1870047 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) followed 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-88b4a36ca38c4b45a7b831082598860d
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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