Toluene → HCID 23114270, compound

HRID 2376275Notes

Reaction equation

HRID 2376275 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)([CH3:11])[CH2:9][OH:10])[C:5](O)=[C:4]([CH3:22])[C:3]=1[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>C1COCC1>[Br:1][C:2]1[C:3]([CH3:23])=[C:4]([CH3:22])[C:5]2[O:10][CH2:9][C:8]([C:12]3[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=3)([CH3:11])[C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 23114021HCID 23114021, compound

Product 1

HCID 23114270HCID 23114270, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-6-(2-hydroxy-1-(4-isopropylphenyl)-1-methylethyl)-2,3-dimethylphenol obtained in Reference Example 22 (830 mg, 2.21 mmol) and triphenylphosphine (638 mg, 2.43 mmol) in THF (60 mL) was added diethylazodicarboxylate (a 40% toluene solution, 1.06 g, 2.43 mmol) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was concentrated under reduced pressure to obtain a residue, which was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain oily 5-bromo-3-(4-isopropylphenyl)-3,6,7-trimethyl-2,3-dihydro-1-benzofuran 660 mg. To a solution of said compound (660 mg, 1.84 mmol) and benzylamine (0.24 mL, 2.21 mmol) in toluene (10 mL) were added palladium acetate (4 mg, 0.02 mmol) and BINAP (34 mg, 0.6 mmol) at room temperature, and the mixture was stirred under argon stream for 15 minutes. Sodium tert-butoxide (248 mg, 2.58 mmol) was added to the reaction solution at room temperature, and the mixture was heated under argon stream for 18 hours. Water was added to the reaction solution, which was extracted with ethyl acetate, the organic layer was washed with water and a saturated brine and then was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1), to obtain 660 mg (yield 77%) of the title compound as an oily matter.

Workup

  1. temperaturecooling
  2. concentrationThe solvent was concentrated under reduced pressure
  3. customto obtain a residue, which
  4. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-394a9563f7de4f0bbc4533f0e8385edf
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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