Formamide → 1-Phenylethanol

HRID 2229895Notes

Reaction equation

HRID 2229895 reaction equation
[C:1]1(NC(=O)[C@@H]2CCCN2C=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17](N)=[O:18].[CH:20](N1CCCC1)=O>>[C:1]1([CH:17]([OH:18])[CH3:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 773721-PyrrolidinecarboxaldehydeHCID 12174323HCID 12174323, compound

Product 1

HCID 74091-PhenylethanolYield 99%

Procedure

The operation was conducted in the same manner as in Example 1 but using an N-phenyl-1-formyl-(S)-prolineamide which was an amide compound having an oxo group on a carbon atom at the β-position of the nitrogen atom, as a formamide compound, instead of using the 1-formylpyrrolidine and conducting the reaction for 15 hours. As a result, there was obtained 0.121 g of a 1-phenyl-1-ethanol (yield, 99%). Further, this compound was measured for its optical purity to be 32.5% ee (R).

Workup

  1. customthe reaction for 15 hours

Sources & evidence

ORD record
ord-2c7a4322996c4cee9e1c23523bcfab17
Source dataset
uspto-grants-2002_07
Patent number
US06420613B1

Reaction notes

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