Sodium Hydroxide → (R)-2-(4-chloro-3-fluorophenyl)oxirane

HRID 530588노트

반응식

HRID 530588 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([F:22])[CH:16]=2)[OH:14])(=O)=O)=CC=1.FC1C=CC(C(=O)C)=CC=1C(F)(F)F.[OH-].[Na+]>CCOCC>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@H:13]2[CH2:12][O:14]2)=[CH:16][C:17]=1[F:22]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 6056784'-Fluoro-3'-(trifluoromethyl)acetophenoneHCID 117870261(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate

생성물 1

HCID 94590788(R)-2-(4-chloro-3-fluorophenyl)oxirane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

(R)-2-(4-chloro-3-fluorophenyl)-2-hydroxyethyl 4-methylbenzenesulfonate (prepared as previously described in Example 1 (steps a-b) except substituting 1-(3-chloro-4-fluorophenyl)ethanone for 1-(4-fluoro-3-(trifluoromethyl)phenyl)ethanone, 3.35 g, 9.72 mmol) was dissolved in ether (80 mL) and 2N NaOH solution (25 mL) was added. The mixture was stirred at room temperature for 6 h until all starting material was consumed. The mixture was separated and the ether layer was washed with water. The organic layer was dried with sodium sulfate and solvents were removed to afford (R)-2-(4-chloro-3-fluorophenyl)oxirane as a colorless oil which was dried in vacuum (1.66 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.71-2.80 (m, 1H) 3.18 (dd, J=5.31, 4.04 Hz, 1H) 3.82-3.89 (m, 1H) 7.01-7.12 (m, 2H) 7.39 (dd, J=8.46, 7.45 Hz, 1H).

후처리

  1. customwas consumed
  2. customThe mixture was separated
  3. washthe ether layer was washed with water
  4. dry with materialThe organic layer was dried with sodium sulfate and solvents
  5. customwere removed

출처 및 근거

ORD 기록
ord-226c60bdf29f44469e0c0d048a6b01b2
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353096B2

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