Vinyl Acetate → (1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate

HRID 1453801노트

반응식

HRID 1453801 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([OH:15])[CH3:14])[CH: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[CH: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]

참가 물질

4

반응물 2

HCID 7904Vinyl AcetateHCID 57528604HCID 57528604, 화합물

생성물 1

HCID 44605723(1R)-1-[5-(3-chlorophenyl)isoxazol-3-yl]ethyl acetate수율 47%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

1-[5-(3-chlorophenyl)isoxazol-3-yl]ethanol (106.5 g, 476 mmol) and Novozyme 435® (13 g) are taken up under Ar in dry toluene (1.5 L). After addition of vinyl acetate (66 mL, 716 mmol) the reaction was run at r.t. over night, followed by filtration over celite and washing with DCM. The solvent was evaporated in vacuo and the crude product was subjected to column chromatography on silica using dichloromethane/methanol=20:1, to give the title compound (50 g, 47%). 1H NMR: 7.76 (m, 1H), 7.65 (m, 1H), 7.41 (m, 2H), 6.54 (s, 1H), 6.07 (q, 1H), 2.13 (s, 3H), 1.66 (d, 3H). LC-MS (M++1)=266.

후처리

  1. waitwas run at r.t. over night
  2. filtrationfollowed by filtration over celite
  3. washwashing with DCM
  4. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-ca5a3222dadc434bb64cc7df8a7e0e49
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476684B2

반응 노트

불러오는 중…