Phosphate → (R)-Phenylacetylcarbinol

HRID 1770066Notes

Reaction equation

HRID 1770066 reaction equation
C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.FC(F)(F)[C:47]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:48].P([O-])([O-])([O-])=O.[OH-].[Na+].C([O:66][CH2:67][CH3:68])C>CCCCCC.CC(O)C>[OH:48][C@H:47]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:67](=[O:66])[CH3:68]

Participants

8

Reactant 5

HCID 1061PhosphateHCID 3283Diethyl EtherHCID 99052,2,2-TrifluoroacetophenoneHCID 14798Sodium HydroxideHCID 439153Nadh

Product 1

HCID 9920426(R)-Phenylacetylcarbinol

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8058HexaneSolvent2×

Procedure

A reaction mixture was formed by admixing (i) 50 mg NAD, (ii) 4 ml of 2-propanol and (iii) 5 mmoles of 1-phenyl-1,2-propanedione, Compound 3, in a liquid medium containing 1 gm of lyophilized PED alcohol dehydrogenase preparation, 75 ml of 50 mM phosphate buffer, pH 7.1, and 25 ml of hexane. The pH value of the reaction was maintained constant by addition of 1N NaOH. The reaction mixture was maintained at room temperature until product formation stopped. When product formation stopped, (R)-1-hydroxy-1-phenyl-2-propanone, Compound 3a, was isolated by removal of the hexane layer and extraction of the aqueous layer with ethyl ether (3×75 ml).

Workup

  1. customA reaction mixture was formed
  2. additionin a liquid medium containing

Sources & evidence

ORD record
ord-11bade5112044762aecc43a40ebd8796
Source dataset
uspto-grants-1995_01
Patent number
US05385833

Reaction notes

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