HCID 18445387, compound → HCID 18445388, compound

HRID 460294Notes

Reaction equation

HRID 460294 reaction equation
[CH3:1][C:2]1([CH3:15])[C:6]2[CH:7]=[C:8]([CH:11]([OH:14])[CH2:12][CH3:13])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:15][C:2]1([CH3:1])[C:6]2[CH:7]=[C:8]([C:11](=[O:14])[CH2:12][CH3:13])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 18445387HCID 18445387, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18445388HCID 18445388, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-propan-1-ol (2.6 g, 12.60 mmol) in dry dichloromethane (40 mL) was added at room temperature pyridinium chlorochromate (3 g, 13.86 mmol). The reaction mixture was stirred for 1 hour at room temperature then filtered over celite. Water was added and the layers separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel (5% ethyl acetate in hexane) to give 530 mg of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-propan-1-one (58%). 1H NMR (300 MHz; CDCl3): δ 1.21 (t, J=7.2 Hz, 3H), 1.37 (s, 6H), 2.94 (q, J=7.2 Hz, 2H), 4.32 (s, 2H), 6.80 (d, J=8.4 Hz, 1H), 7.79 (s, 1H), 7.81 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationthen filtered over celite
  2. additionWater was added
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted twice with dichloromethane
  5. washThe combined organic layers were washed successively with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b9ef35d9b3ed4dd5a790c3ea96c5fe08
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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