tert-Butanol → HCID 54265450, compound

HRID 1783547Notes

Reaction equation

HRID 1783547 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([O:13][CH3:14])=[CH:7][C:3]=1C(O)=O.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([O:13][CH3:14])=[CH:7][C:3]=1[NH:17][C:20](=[O:29])[O:43][C:39]([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 543612282-Chloro-3,5-dimethoxybenzoic acid

Product 1

HCID 54265450HCID 54265450, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a solution of 9.57 g (44.18 mmol) of 2-chloro-3,5-dimethoxy-benzoic acid and 4.78 g (47.3 mmol) of triethylamine in 250 mL of toluene was added 13.57 g (49.3 mmol) diphenylphosphoryl azide. The reaction was refluxed for 4 hours. To the reaction was added 3.63 g (49.0 mmol) of tert-butanol. The reaction was refluxed overnight then concentrated in vacuo. The residue was partitioned between a cold 1N solution of citric acid and ethyl acetate. The ethyl acetate layer was washed twice with each of the following: cold IN citric acid solution, water, and then saturated sodium bicarbonate solution. The ethyl acetate layer was dried with magnesium sulfate and concentrated in vacuo. The residue was dissolved in tetrahydrofuran, added silica gel and concentrated to dryness. The residue was chromatographed on silica gel, eluting with hexane/diethyl ether (9:1 v/v), to give 8.14 g (64%) of the title compound: mp 94.5-95.5° C.

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. temperatureThe reaction was refluxed overnight
  3. concentrationthen concentrated in vacuo
  4. customThe residue was partitioned between a cold 1N solution of citric acid and ethyl acetate
  5. washThe ethyl acetate layer was washed twice with each of the following: cold IN citric acid solution, water
  6. dry with materialThe ethyl acetate layer was dried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in tetrahydrofuran
  9. additionadded silica gel
  10. concentrationconcentrated to dryness
  11. customThe residue was chromatographed on silica gel
  12. washeluting with hexane/diethyl ether (9:1 v/v)

Sources & evidence

ORD record
ord-4c3a6f3ab0ce4779a84e24dab0f73ba6
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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