Water → (R)-2-phenyl-1,2-propanediol

HRID 37021

反応式

HRID 37021 の反応式
OP(O)(O)=O.[OH2:6].C([O-])([O-])=[O:8].[K+].[K+].[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH2:15]>[Pt].O=[Os](=O)(=O)=O.CC(O)(C)C>[C:16]1([C@:14]([OH:8])([CH3:13])[CH2:15][OH:6])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

8

反応物 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 7407Alpha-Methylstyrene2 回HCID 11430Potassium Carbonate

生成物 1

HCID 6951538(R)-2-phenyl-1,2-propanediol収率 95%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 30318Osmium Tetroxide触媒HCID 6386tert-Butanol溶媒

実験手順

A flow cell reactor filled with a 100 cm2 platinum on titanium anode and a 100 cm2 stainless steel cathode--the two electrode compartment being divided by a Nafion® cation exchange membrane--is used. A solution of 5% H3PO4 is circulated through the cathode compartment, while a solution of anolyte consisting of the followings: H2O (2 liters), t-BuOH (2 liters), K3Fe(CN)6 (0.24 mole, 91 g), K2CO3 (4.8 mole, 662 g), the chiral ligand, PHAL-DHQD (0.012 mole, 9.3 g), OsO4 (0.2M in toluene, 0.0008 mole, 4 mL) and α-methylstyrene (1.6 mole, 189 g) is circulated through the anode compartment. A constant current of 3 A (current density 30 mA/cm2) is applied at 15° C. until almost all the α-methylstyrene is consumed (the reaction is followed by thin layer chromatography on silica gel). The product is isolated as described above (Example 6.1) to provide (R)-2-phenyl-1.2-propanediol in 95% yield and 90% ee.

後処理

  1. customis applied at 15° C.
  2. customis consumed (the reaction
  3. customThe product is isolated

出典と根拠

ORDレコード
ord-c49487e0f3084f19a2d6024d992082a7
出典データセット
uspto-grants-1995_05
特許番号
US05419817

関連ノート

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