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

HRID 1108533Notes

Reaction equation

HRID 1108533 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-075e4a2a5f7d4ec5a2c8904f8657f19a
Source dataset
uspto-grants-2000_05
Patent number
USRE036718

Reaction notes

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