Tetrahydrofuran → HCID 12010830, compound

HRID 1282463Notes

Reaction equation

HRID 1282463 reaction equation
Br[C:2]([CH:16]([CH3:18])[CH3:17])=[C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1COCC1.C([Li])CCC.Cl[P:30]([CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1)[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>O>[C:4]1([C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([P:30]([CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]2)[CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH:16]([CH3:18])[CH3:17])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2734135ChlorodicyclohexylphosphineHCID 18424469HCID 18424469, compoundHCID 178418339Butyllithium

Product 1

HCID 12010830HCID 12010830, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-70 °C

Procedure

Into a reactor were introduced 1.20 g (4.00 mmol) of the 2-bromo-1,1-diphenyl-3-methylbutene and 12 mL of THF under a nitrogen atmosphere. The contents were cooled to −70° C., and 2.8 mL (4.4 mmol; 1.6 M hexane solution) of butyllithium was gradually added dropwise thereto. The resultant mixture was stirred at that temperature for 30 minutes. Thereafter, 1.1 mL (4.8 mmol) of chlorodicyclohexylphosphine was added thereto, and this mixture was stirred at that temperature for 3 hours and then heated to room temperature over 13 hours. Water was added to the reaction mixture. The organic layer was extracted with ethyl acetate, and the extract was dried with anhydrous magnesium sulfate. Thereafter, the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol and toluene to obtain 0.72 g (43%) of the target compound as white crystals.

Workup

  1. temperatureheated to room temperature over 13 hours
  2. extractionThe organic layer was extracted with ethyl acetate
  3. dry with materialthe extract was dried with anhydrous magnesium sulfate
  4. customThereafter, the solvent was removed under reduced pressure
  5. customThe concentrate was recrystallized from ethanol and toluene

Sources & evidence

ORD record
ord-7605a91e523146ff832e16d86c6e8bce
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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