1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-ol → 1-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-one

HRID 460287Notes

Reaction equation

HRID 460287 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]2[CH:7]=[C:8]([CH:11]([OH:15])[CH:12]([CH3:14])[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>[CH3:16][C:2]1([CH3:1])[C:6]2[CH:7]=[C:8]([C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 220414081-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)-2-methyl-propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 184453861-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-oneYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-2-methyl-propan-1-ol (example 1e) (1.13 g, 5.15 mmol) in dry dichloromethane (20 mL) was added at room temperature pyridinium chlorochromate (1.33 g, 6.18 mmol). The reaction mixture was stirred for 2 hours 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)-2-methyl-propan-1-one (47%). 1H NMR (300 MHz; CDCl3): δ 1.21 (d, J=7.2 Hz, 6H), 1.38 (s, 6H), 3.52 (m, 1H), 4.32 (s, 2H), 6.80 (d, J=7.5 Hz, 1H), 7.80 (m, 2H).

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-4ee1845e7ec34b2bb2ce89108b562057
Source dataset
uspto-grants-2007_03
Patent number
US07196108B2

Reaction notes

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