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

HRID 926215Notes

Reaction equation

HRID 926215 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7e3a058b10564f53a2b848883dede2dd
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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