Binol → lanthanum (R)-1,1'-bi-2-naphthol

HRID 52611

Reaction equation

HRID 52611 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][C:9]([OH:22])=[C:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][C:12]=3[OH:21])[C:4]2=[CH:3][CH:2]=1.C([Li])CCC.CC(C)[O-].[La+3:32].CC(C)[O-].CC(C)[O-]>C1COCC1.CCCCCC>[La:32].[CH:17]1[CH:16]=[C:15]2[CH:14]=[CH:13][C:12]([OH:21])=[C:11]([C:10]3[C:4]4[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=4)[CH:7]=[CH:8][C:9]=3[OH:22])[C:20]2=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11762BinolHCID 9858075Lanthanum isopropoxideHCID 178418339Butyllithium

Product 1

HCID 131719953lanthanum (R)-1,1'-bi-2-naphthol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 258 mg (0.90 mmol) of (R)-1,1'-bi-2-naphthol in 4.5 ml of THF Was added dropwise 0.56 ml (0.90 mmol) of a 1.6N n-butyllithium solution in hexane, at 0° C. in an argon atmosphere. After completion of the dropping, the temperature was raised to room temperature, 95 mg (0.30 mmol) of powdery lanthanum isopropoxide was added, and the mixture was stirred at room temperature for 15 hours. The insoluble matter was allowed to precipitate and the supernatant was submitted, as a lanthanum/(R)-1,1'-bi-2-naphthol complex solution (0.05 mol/l), to the reaction proper.

Workup

  1. customat 0° C.
  2. customto precipitate
  3. customthe supernatant was submitted, as a lanthanum/(R)-1,1'-bi-2-naphthol complex solution (0.05 mol/l), to the reaction proper

Sources & evidence

ORD record
ord-22026acd963c477fa474a5b7f1fb1c7d
Source dataset
uspto-grants-1997_04
Patent number
US05616726

Linked notes

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