Tert-Butyl nitrite → ethyl 5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylate

HRID 1809048Notes

Reaction equation

HRID 1809048 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[S:8][C:7]=1N)=[O:5])[CH3:2].N(OC(C)(C)C)=O.[Cl-].[NH4+]>[Cu](Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[S:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 25517Ammonium ChlorideHCID 59542499ethyl 2-amino-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylate

Product 1

HCID 59542513ethyl 5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylateYield 60.6%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

2-Amino-5-(tetrahydro-pyran-4-yl)-thiophene-3-carboxylic acid ethyl ester (1.79 g, 7 mmol) was added to a suspension of tert-butyl nitrite (10.5 mmol) and copper (II) chloride (7 mmol) in IMS (70 mL). The reaction was stirred for 15 minutes then saturated aqueous ammonium chloride (7 mL) was added and the mixture stirred for a further 15 minutes. The solvent was removed under vacuum and the residue partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate, filtered and the solvent evaporated to give the title compound (1.02 g). LCMS m/z 241 [M+H]+ RT=3.44 min (Analytical Method 4).

Workup

  1. stirringthe mixture stirred for a further 15 minutes
  2. customThe solvent was removed under vacuum
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-b621937e0e1d4fd495682b034e9ae1a2
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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