Tetrahydrofuran → Cy-vBRIDP

HRID 1282453Notes

Reaction equation

HRID 1282453 reaction equation
Br[C:2]([CH3:16])=[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:28]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O>[C:4]1([C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([P:28]([CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]2)[CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH3:16])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 2734135ChlorodicyclohexylphosphineHCID 52517812-Bromo-1,1-diphenylpropeneHCID 178418339Butyllithium

Product 1

HCID 12010824Cy-vBRIDPYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-70 °C

Procedure

Into a reactor were introduced 8.50 g (31.1 mmol) of the 2-bromo-1,1-diphenylpropene obtained in Example 1 (2) and 85 ml of THF under a nitrogen atmosphere. The contents were cooled to −70° C. Thereto was gradually added dropwise 21.4 mL (34.2 mmol; 1.6 M hexane solution) of butyllithium. The resultant mixture was stirred for 30 minutes. Thereafter, 8.25 mL (37.3 mmol) of chlorodicyclohexylphosphine was added, and this mixture was stirred for 75 minutes, subsequently heated to room temperature, and then further stirred for 15.5 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 to obtain 8.80 g (72%) of the target compound as white crystals.

Workup

  1. temperaturesubsequently heated to room temperature
  2. stirringfurther stirred for 15.5 hours
  3. extractionThe organic layer was extracted with ethyl acetate
  4. dry with materialthe extract was dried with anhydrous magnesium sulfate
  5. customThereafter, the solvent was removed under reduced pressure
  6. customThe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-ff52422c707d46f8a6cbfbf541aa34ac
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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