Phosphate → 1-Phenylethanol, (R)-

HRID 1770065Notes

Reaction equation

HRID 1770065 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.F[C:46](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(OCC)C.CCCCCC.CC(O)C>[C:49]1([C@H:47]([OH:48])[CH3:46])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

8

Reactant 4

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

Product 1

HCID 6375161-Phenylethanol, (R)-

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 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 acetophenone, Compound 2, 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 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-Phenylethanol, Compound 2a, 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-d2ea58b68ecd4c4fa98e5df479047505
Source dataset
uspto-grants-1995_01
Patent number
US05385833

Reaction notes

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