Vinyl Acetate → HCID 59424210, 화합물

HRID 639836

반응식

HRID 639836 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N: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].C(CC([O-])=O)=C>C1(C)C=CC=CC=1>[C:16]([O:15][C@@H:13]([C:10]1[N:11]=[N:12][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)[CH3:14])(=[O:18])[CH3:17]

참가 물질

5

반응물 3

HCID 7904Vinyl AcetateHCID 69710893-Butenoic acid, ion(1-)3회HCID 594242172-(3-chloro-phenyl)-2H-tetrazol-5-yl-ethanol

생성물 1

HCID 59424210HCID 59424210, 화합물수율 400.4%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
30 °C

실험 절차

2.22 g (9.93 mmol) racemic 1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethanol and 0.40 g Novozyme 435® are taken up under Ar in toluene (120 mL). After addition of 109 μL (1.18 mmol) vinyl acetate the reaction was run at r.t. o.n., followed by addition of 0.12 g Novozyme 435® and 218 μL (2.36 mmol) vinylacetate and increasing the temperature to 30° C. o.n. Further addition of 2 g Novozyme 435® and 150 μL (1.63 mmol) vinylacetate gave after 7 h ca 41% conversion of starting material. To enhance yield, the reaction was filtered over celite washed with DCM, evaporated to dryness, then taken up in toluene (250 mL). After addition of 0.3 g Novozyme 435® and 200 μL (2.17 mmol) vinylacetate under Ar, 48% conversion after 4 h at r.t. were achieved. Filtration over celite and washing with DCM gave crude which was purified over silica using DCM neat, followed by EA/Hep=1/2, yielding 1.26 g (48%) of the title compound. 1H NMR: 8.15 (m, 1H), 8.03 (m, 1H), 7.48 (m, 2H), 6.27 (q, 1H), 2.14 (s, 3H), 1.77 (d, 3H).

후처리

  1. customwas run at r.t.
  2. customgave after 7 h ca 41% conversion of starting material
  3. customTo enhance yield
  4. filtrationthe reaction was filtered
  5. washover celite washed with DCM
  6. customevaporated to dryness
  7. filtrationFiltration over celite
  8. washwashing with DCM
  9. customgave crude which
  10. customwas purified over silica

출처 및 근거

ORD 기록
ord-c0e8498c0e2843bea78a3cb3a4256c7e
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691892B2

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