Quinone → (S)-2-isopropenyl-2-methyl-2,3-dihydrobenzofuran

HRID 1374131

Reaction equation

HRID 1374131 reaction equation
C1(C2C3C(=CC=CC=3)C=CC=2)C2C(=CC=CC=2)C=CC=1.O1CCN=C1.[CH3:26][C:27](=[C:36]([CH3:38])[CH3:37])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[OH:35].C1(=O)C=CC(=O)C=C1>[Pd].CO>[C:36]([C@:27]1([CH3:26])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35]1)([CH3:38])=[CH2:37]

Participants

7

Reactant 4

HCID 4650QuinoneHCID 117891,1'-BinaphthylHCID 68157OxazolineHCID 117451632-(2,3-Dimethyl-2-butenyl)phenol

Product 1

HCID 11095126(S)-2-isopropenyl-2-methyl-2,3-dihydrobenzofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A polymer-carrying optically active binaphthyl type oxazoline compound-palladium complex (palladium content, 0.02 mmol), 35.2 mg (0.2 mmol) of 2-(2,3-dimethyl-2-butenyl)-phenol and 86.4 mg (0.8 mmol) of benzoquinone were added to 1 ml of methanol and then stirred at 60° C. for 20 hours. After cooling to room temperature, the resin was filtered and washed twice with 1 ml of methanol. The solution was concentrated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=95/5) to obtain (S)-2-isopropenyl-2-methyl-2,3-dihydrobenzofuran as a colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resin was filtered
  3. washwashed twice with 1 ml of methanol
  4. concentrationThe solution was concentrated under a reduced pressure
  5. customthe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-76514e6f8aa3495089a0a80be597a13a
Source dataset
uspto-grants-2007_01
Patent number
US07164026B2

Linked notes

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