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

HRID 926215ノート

反応式

HRID 926215 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-7e3a058b10564f53a2b848883dede2dd
出典データセット
uspto-grants-2016_03
特許番号
US09284323B2

反応ノート

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