Sodium Nitrite → HCID 86718008, compound

HRID 1500470Notes

Reaction equation

HRID 1500470 reaction equation
[CH3:1][C@@H:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:4]=2[O:3]1.[N:12]([O-:14])=[O:13].[Na+]>C(O)(C(F)(F)F)=O>[CH3:1][C@@H:2]1[CH2:6][C:5]2[CH:7]=[C:8]([CH3:11])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 86718007HCID 86718007, compound

Product 1

HCID 86718008HCID 86718008, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (R)-2,5-dimethyl-2,3-dihydrobenzofuran (3d) (2.0 g, 13 mmol) in TFA (40 mL) was cooled to 0° C., NaNO2 (1.7 g, 23 mmol) was added thereto. It was stirred at ambient temperature for 12 h. The mixture was concentrated, poured into water (50 mL), extracted with EtOAc (150 mL), washed with brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1) to give the title compound (3e).

Workup

  1. concentrationThe mixture was concentrated
  2. additionpoured into water (50 mL)
  3. extractionextracted with EtOAc (150 mL)
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1)

Sources & evidence

ORD record
ord-b6a2dfdc30224808820956b1bf791b10
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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