Naphthalene → HCID 59216880, compound

HRID 2245745Notes

Reaction equation

HRID 2245745 reaction equation
[C:1]1([P:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:9]2[C:10]([CH3:31])=[C:11]3[C:15](=[C:16]([CH3:30])[C:17]=2[C:18]2[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][C:19]=2[O:28][CH3:29])[CH2:14][O:13][CH2:12]3)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C1C2C(=CC=CC=2)C=CC=1.Cl[SiH](Cl)Cl.C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1.C(OCC)C>[C:32]1([P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:9]2[C:10]([CH3:31])=[C:11]3[C:15](=[C:16]([CH3:30])[C:17]=2[C:18]2[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][C:19]=2[O:28][CH3:29])[CH2:14][O:13][CH2:12]3)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 931NaphthaleneHCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 516892Sodium BicarbonateHCID 59216873HCID 59216873, compound

Product 1

HCID 59216880HCID 59216880, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
4 °C

Procedure

(−)-5-(Diphenylphosphinoyl)-6-(2-methoxynaphthalen-1-yl)-4,7-dimethyl-1,3-dihydroisobenzofuran (800 mg, 1.59 mmol, 92% ee) was placed into a flask and the atmosphere in the flask was replaced with nitrogen. Triethylamine (4.4 mL, 31.8 mmol) was added to a solution of this naphthalene compound in xylene (40 mL), and cooled to 4° C. Further, trichlorosilane (800 μL, 7.95 mmol) was added dropwise, and the mixture was stirred for 30 minutes and then stirred at room temperature for 15 minutes. Further, the reaction mixture was heated to 110° C. and stirred for 3 hours. After the resulting reaction mixture was cooled to room temperature, diethyl ether (60 mL) and saturated aq. sodium bicarbonate (800 μL) were added, and the mixture was stirred for 30 minutes. The reaction mixture was filtered through Celite, and after the filtrate was dried with sodium sulfate. After silica gel was added, the mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain the title compound (694 mg, 89%, 92% ee).

Workup

  1. stirringstirred at room temperature for 15 minutes
  2. temperatureFurther, the reaction mixture was heated to 110° C.
  3. stirringstirred for 3 hours
  4. customAfter the resulting reaction mixture
  5. temperaturewas cooled to room temperature
  6. stirringthe mixture was stirred for 30 minutes
  7. filtrationThe reaction mixture was filtered through Celite
  8. dry with materialafter the filtrate was dried with sodium sulfate
  9. additionAfter silica gel was added
  10. concentrationthe mixture was concentrated under reduced pressure
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-abbcf75f03754d40aebd3c4a6a367f2b
Source dataset
uspto-grants-2010_03
Patent number
US07683186B2

Reaction notes

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