Isopropyl methanesulfonate → 3-Isopropyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol

HRID 1790997ノート

反応式

HRID 1790997 の反応式
[C:1]1([OH:21])[C:2]([C:11]2[CH:20]=[CH:19][C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:12]=2)=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.CS(O[CH:27]([CH3:29])[CH3:28])(=O)=O>[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.C(Cl)(Cl)(Cl)Cl>[CH:27]([C:3]1[CH:4]=[C:5]2[C:10]([CH2:9][CH2:8][CH2:7][CH2:6]2)=[C:1]([OH:21])[C:2]=1[C:11]1[CH:20]=[CH:19][C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:29])[CH3:28]

参加物

5

反応物 2

HCID 13551Isopropyl methanesulfonateHCID 220441995,5',6,6',7,7',8,8'-Octahydro-2,2'-binaphthol

生成物 1

HCID 220441953-Isopropyl-5,5',6,6',7,7',8,8'-octahydro-2,2'-binaphthol収率 78%

試薬・触媒・溶媒 2

HCID 2734571Scandium(III) triflate触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol (2 g, 6.8 mmol), isopropyl methanesulfonate (5.5 mmol), scandium triflate (0.34 g, 5 mol %), and carbon tetrachloride (10 ml) was brought to reflux under argon. After 18 hours, GC indicated 65% conversion to give 78% desired product. Additional isopropyl methanesulfonate (3.1 mmol) was added, and the reaction mixture was refluxed for another 8 hours. GC showed 86% conversion, and 76% selectivity to 3-isopropyl-5,5′,6,6′,7,7′,8,8′-octahydro-2,2′-binaphthol. The mixture was diluted with ether (20 ml) and 10% HCl (20 ml). The layers were separated, and the aqueous layer was extracted with ether (3×20 ml). The ether layers were combined, dried (MgSO4), and concentrated. The crude product was purified by column chromatography (SiO2, 2% ethyl acetate/hexanes) to yield 1.1 g white solid (48%). MP: 100–102° C.

後処理

  1. temperatureto reflux under argon

出典と根拠

ORDレコード
ord-04a94cb311e24ec1addae5f01600a743
出典データセット
uspto-grants-2006_07
特許番号
US07071365B2

反応ノート

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