Acetophenone → HCID 131732618, compound

HRID 878934Notes

Reaction equation

HRID 878934 reaction equation
[Ru:1].[Ru].[Cl-:3].[NH4+].[C:5]1([C@H:11]([NH:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C@H:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20](C)[CH:19]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:42](C1C=CC=CC=1)(=O)C.C1([C@@H](O)C)C=CC=CC=1>C(N(CC)CC)C.C(O)=O>[Ru:1].[Cl-:3].[NH4+:13].[C:5]1([C@H:11]([NH:31][S:32]([C:35]2[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=2)(=[O:33])=[O:34])[C@H:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH3:42])=[CH:22][CH:23]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7410AcetophenoneHCID 23950RutheniumHCID 4431351-Phenylethanol, (S)-HCID 131732619HCID 131732619, compound

Product 1

HCID 131732618HCID 131732618, compound

Reagents, catalysts & solvents 1

HCID 11084032Triethylammonium formateSolvent

Procedure

In a 25-ml Schlenk tube, 4.9 mg (0.00339 mmol, S/C=1000) of the ruthenium dimer complex produced in Example 5, acetophenone (0.82 g, 6.86 mmol), and 3.4 ml of a formic acid-triethylamine (5:2) azeotrope were mixed with each other, and the reaction was allowed to proceed at 60° C. for 5 hours. GC analysis of the reaction liquid showed that (S)-1-phenylethanol was formed with a conversion of 98.9% and 96.6% ee.

Workup

  1. customGC analysis of the reaction liquid
  2. customwas formed with a conversion of 98.9% and 96.6% ee

Sources & evidence

ORD record
ord-98611643134143cea3d7df99fa8ee6f8
Source dataset
uspto-grants-2015_03
Patent number
US08987492B2

Reaction notes

Loading…