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Tetrahydrofuran → 1,1-Diphenyl-2-(diphenylphosphino)propene

HRID 1282452
Notes
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Reaction equation

HRID 1282452 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]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH: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]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:16])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 66180ChlorodiphenylphosphineHCID 52517812-Bromo-1,1-diphenylpropeneHCID 178418339Butyllithium

Product 1

HCID 120108231,1-Diphenyl-2-(diphenylphosphino)propeneYield 60%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
-70 °C

Procedure

Into a reactor were introduced 1.37 g (5.00 mmol) of the 2-bromo-1,1-diphenylpropene and 14 mL of THF under a nitrogen atmosphere. The contents were cooled to −70° C., and 3.4 mL (5.5 mmol; 1.6 M hexane solution) of butyllithium was gradually added dropwise thereto. The resultant mixture was stirred for 30 minutes. Thereafter, 1.1 mL (6.0 mmol) of chlorodiphenylphosphine was added, and this mixture was heated to room temperature and then stirred for 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 to obtain 1.08 g (60%) of the target compound as white crystals.

Workup

  1. temperaturethis mixture was heated to room temperature
  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

Sources & evidence

ORD record
ord-13f6c42240234d98b1f1d4f6297d04b4
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06455720B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes