Ethyl Acetate → HCID 18000280, compound

HRID 324572Notes

Reaction equation

HRID 324572 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15].[N-:17]=[N+:18]=[N-:19].[Na+].C(OCC)(=O)C>CN(C=O)C>[N:17]([CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 28008916-(Chloromethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 18000280HCID 18000280, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloromethyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (10 g, 42.2 mmol, 1.00 mmol equiv.) in DMF (84 mL) is added sodium azide (13.7 g, 211.2 mmol, 5.00 mmol equiv.) at room temperature and the reaction contents are stirred overnight. The reaction is checked by TLC (5% ethyl acetate in hexanes). The reaction is terminated by pouring the reaction contents into water and extracting with ethyl acetate. The organic solvents are removed in vacuo and the crude product filtered through a plug of silica gel (ratio of 10:1) and eluted with hexanes. The solvent is removed in vacuo and stored under vacuo to afford 10 grams of the desired product 6-azidomethyl-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (97% yield).

Workup

  1. customthe reaction contents
  2. customThe reaction is terminated
  3. additionby pouring
  4. customthe reaction contents into water
  5. extractionextracting with ethyl acetate
  6. customThe organic solvents are removed in vacuo
  7. filtrationthe crude product filtered through a plug of silica gel (ratio of 10:1)
  8. washeluted with hexanes
  9. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-116506d1837b4b48ad4f79f86a7548b2
Source dataset
uspto-grants-2001_04
Patent number
US06218426B1

Reaction notes

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