Potassium tert-butoxide → (R)-2-(1-chloro-3-methylnaphthalen-2-yl)oxirane

HRID 926215노트

반응식

HRID 926215 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[C:24]([CH3:25])=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[Cl:26])[OH:14])(=O)=O)=CC=1.CC(C)([O-])C.[K+]>C1COCC1>[Cl:26][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[C:24]([CH3:25])[C:15]=1[C@@H:13]1[CH2:12][O:14]1

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 89676690(R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

생성물 1

HCID 89676658(R)-2-(1-chloro-3-methylnaphthalen-2-yl)oxirane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate (1.38 g, 3.54 mmol) in THF (39 mL) at 0° C. was added potassium tert-butoxide (3.90 mL of 1.0 M solution in THF, 3.90 mmol). After stirring for 1 h, the reaction mixture was quenched with saturated aqueous NH4Cl, and then diluted with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes) to give (R)-2-(1-chloro-3-methylnaphthalen-2-yl)oxirane. 1H-NMR: 400 MHz, (CDCl3) δ 8.26 (d, J=8.4 Hz, 1H), 7.74 (d, J=7.6 Hz, 1H), 7.57-7.48 (m, 3H), 4.13 (t, J=3.6 Hz, 1H), 3.34 (t, J=5.6 Hz, 1H), 2.97 (dd, J=5.2, 2.8 Hz, 1H), 2.64 (s, 3H).

후처리

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-7e3a058b10564f53a2b848883dede2dd
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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