Acetophenone → HCID 131732620, compound

HRID 878935Notes

Reaction equation

HRID 878935 reaction equation
[Ru:1].[Ru].[Cl-:3].[NH4+].[C:5]1([C@H:11]([NH:31][S:32]([CH3:35])(=[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]C2C=CC=C(C)C=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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]([CH3:35])(=[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:42]2[CH:43]=[CH:44][C:39]([CH3:36])=[CH:40][CH:41]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7410AcetophenoneHCID 23950RutheniumHCID 4431351-Phenylethanol, (S)-HCID 131732621HCID 131732621, compound

Product 1

HCID 131732620HCID 131732620, compound

Reagents, catalysts & solvents 1

HCID 11084032Triethylammonium formateSolvent

Procedure

In a 25-ml Schlenk tube, 4.4 mg (0.00341 mmol, S/C=1000) of the ruthenium dimer complex produced in Example 9, 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 99.2% and 95.0% ee.

Workup

  1. customGC analysis of the reaction liquid
  2. customwas formed with a conversion of 99.2% and 95.0% ee

Sources & evidence

ORD record
ord-937ef8795f13438588acaa09c67a5f24
Source dataset
uspto-grants-2015_03
Patent number
US08987492B2

Reaction notes

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