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

HRID 52612

反応式

HRID 52612 の反応式
[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

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4ab3c2df33f4421996d30d0573499648
出典データセット
uspto-grants-1997_04
特許番号
US05616726

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