Water → samarium (R)-1,1'-bi-2-naphthol

HRID 1108534

Reaction equation

HRID 1108534 reaction equation
[Cl-].[Cl-].[Cl-].[Sm+3:4].[Li].C([Li])CCC.[CH:11]1[CH:16]=[C:15]2[CH:17]=[CH:18][C:19]([OH:32])=[C:20]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][C:22]=3[OH:31])[C:14]2=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+].O>C1COCC1.CCCCCC>[Sm:4].[CH:27]1[CH:26]=[C:25]2[CH:24]=[CH:23][C:22]([OH:31])=[C:21]([C:20]3[C:14]4[C:15](=[CH:16][CH:11]=[CH:12][CH:13]=4)[CH:17]=[CH:18][C:19]=3[OH:32])[C:30]2=[CH:29][CH:28]=1

Participants

9

Reactant 6

HCID 962WaterHCID 11762BinolHCID 3028194LithiumHCID 10131313Samarium(3+);trichlorideHCID 23676156Sodium t-butoxideHCID 178418339Butyllithium

Product 1

HCID 92015231samarium (R)-1,1'-bi-2-naphthol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

To a suspension of 128 mg (0.50 mmol) of anhydrous samarium trichloride (SmCl3) in 4.0 ml of THF were added, in an argon atmosphere at room temperature, a lithium binaphthoxide solution in THF [prepared by adding 1.25 ml (2.0 mmol) of a 1.6N n-butyllithium solution in hexane to a solution of 286.4 mg (1.0 mmol) of (R)-1,1'-bi-2-naphthol in 4.0 ml of THF], 48.1 mg (0.50 mmol) of sodium t-butoxide and 99 μl (5.5 mmol) of water, in that order, and the mixture was stirred at room temperature for 15 hours and then allowed to stand overnight to allow the insoluble matter to precipitate. The supernatant solution was submitted to the reaction proper as a samarium/(R)-1,1'-bi-2-naphthol complex solution (0.05 mmol/l).

Workup

  1. additionwere added, in an argon atmosphere at room temperature
  2. waitto stand overnight
  3. customto precipitate
  4. customThe supernatant solution was submitted to the reaction proper as a samarium/(R)-1,1'-bi-2-naphthol complex solution (0.05 mmol/l)

Sources & evidence

ORD record
ord-13a51c2fd9064fb4ad338d07e58c5a99
Source dataset
uspto-grants-2000_05
Patent number
USRE036718

Linked notes

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