tert-Butanol → HCID 18966278, compound

HRID 2226098Notes

Reaction equation

HRID 2226098 reaction equation
[CH3:1][C:2]1([CH3:15])[O:6][C:5]2[CH:7]=[CH:8][C:9]([F:14])=[C:10](C(O)=O)[C:4]=2[O:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.C([N:35]([CH2:38]C)CC)C.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>>[CH3:15][C:2]1([CH3:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([F:14])=[C:10]([NH:35][C:38](=[O:23])[O:44][C:40]([CH3:43])([CH3:42])[CH3:41])[C:4]=2[O:3]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 189662885-Fluoro-2,2-dimethyl-2H-1,3-benzodioxole-4-carboxylic acid

Product 1

HCID 18966278HCID 18966278, compound

Procedure

In a flask were placed 10 g (0.047 mole) of 2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-ylcarboxylic acid, 12.98 g (0.0471 mole) of diphenylphosphoryl azide, 4.77 g (0.0471 mole) of triethylamine, and 80 mL of t-butanol. This mixture was heated at reflux for approximately 16 hours, after which the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel, eluting first with a ;methylene chloride/heptane mixture and finally with pure methylene chloride. The product-containing fractions were combined, and the solvents were evaporated under reduced pressure, leaving 11.9 g of t-butyl N-(2,2-dimethyl-5-fluoro-1,3-benzodioxol-4-yl)carbamate as a residue, mp 106-107° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask were placed
  2. temperatureThis mixture was heated
  3. temperatureat reflux for approximately 16 hours
  4. customafter which the solvent was evaporated under reduced pressure
  5. washeluting first with a
  6. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-dec895579dc64490ae4c942a9c81c42b
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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