5-Methyl-2,3-dihydro-1-benzofuran → HCID 86718001, compound

HRID 1500461Notes

Reaction equation

HRID 1500461 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[N:11]([O-:13])=[O:12].[Na+]>C(O)(C(F)(F)F)=O>[CH3:1][C:2]1[CH:3]=[C:4]([N+:11]([O-:13])=[O:12])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 127251905-Methyl-2,3-dihydro-1-benzofuranHCID 23668193Sodium Nitrite

Product 1

HCID 86718001HCID 86718001, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-methyl-2,3-dihydrobenzofuran (1b) (2.7 g, 20 mmol) in TFA (50 mL) was cooled to 0° C., NaNO2 (2.5 g, 36 mmol) was added thereto. Then it was warmed up to ambient temperature and stirred 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 (10:1) to give the title compound (1c).

Workup

  1. temperatureThen it was warmed up to ambient temperature
  2. concentrationThe mixture was concentrated
  3. additionpoured into water (50 mL)
  4. extractionextracted with EtOAc (150 mL)
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1)

Sources & evidence

ORD record
ord-6949c88b848e4ddb865888bb1182c9e4
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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