tert-Butanol → HCID 10584705, compound

HRID 388941Notes

Reaction equation

HRID 388941 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1C(O)=O.C1(P([N:24]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:27]([OH:31])([CH3:30])([CH3:29])[CH3:28].[O:32]1[CH2:37]COCC1>O>[C:27]([O:31][C:37](=[O:32])[NH:24][C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 312751,4-DioxaneHCID 902693-Methyl-2-thenoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 10584705HCID 10584705, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-methylthiophene-2-carboxylic acid (7 mmol) in anhydrous dioxane (20 mL) was added diphenyl phosphoryl azide (7 mmol), tert-butanol (6 mL) and TEA (1 mL). The resulting mixture was stirred at reflux for 16 h. The reaction mixture was cooled to room temperature, diluted with H2O (40 mL), and was extracted with EtOAc (3×20 mL). The combined extracts were dried (MgSO4) and the solvent was removed in vacuo. The residue obtained was purified by flash column chromatography using hexanes/EtOAc (7:3) as eluent to afford (3-methylthiophen-2-yl)-carbamic acid tert-butyl ester.

Workup

  1. temperatureat reflux for 16 h
  2. extractionwas extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customthe solvent was removed in vacuo
  5. customThe residue obtained
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-36b607fd4539403d9240b193cf27ea44
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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