Vinyl Acetate → (+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl acetate

HRID 732122Notes

Reaction equation

HRID 732122 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([OH:15])[CH3:14])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:16](OC=C)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1>[C:16]([O:15][C@@H:13]([C:10]1[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][N:11]=1)[CH3:14])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

Product 1

HCID 57837970(+)-(1R)-1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethyl acetateYield 49.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

12.1 g (53.9 mmol) 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol an 1.60 g Novozyme 435® are taken up under Ar in toluene (750 mL). After addition of 5.0 mL (54.2 mmol) vinyl acetate the reaction was run at r.t. o.n., followed by filtration over celite and washing with DCM. The filtrate was purified over silica using DCM neat, followed by EA/Hep=1/1, yielding 7.1 g (49%) of the title compound. 1H NMR: 8.13 (t, 1 H), 8.01 (d, 1 H), 7.55 (d, 1 H), 7.47 (t, 1 H), 6.07 (q, 1 H), 2.15 (s, 3 H), 1.69 (d, 3 H)

Workup

  1. customwas run at r.t.
  2. filtration, followed by filtration over celite
  3. washwashing with DCM
  4. customThe filtrate was purified over silica

Sources & evidence

ORD record
ord-3bdb7924ac324bfd85b0897286f0dab9
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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