Ammonium Chloride → 3-(1,3-Dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

HRID 626082노트

반응식

HRID 626082 반응식
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][CH:3]=1.[O:14]1[CH2:19][CH2:18][CH2:17][O:16][CH:15]1[CH2:20][CH2:21][Mg]Br.[NH4+].[Cl-]>C1COCC1>[O:14]1[CH2:19][CH2:18][CH2:17][O:16][CH:15]1[CH2:20][CH2:21][C:6]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:13][CH:12]=1)=[O:7]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 140693474-Fluoro-N-methoxy-N-methylbenzamideHCID 178419673HCID 178419673, 화합물2회

생성물 1

HCID 247278283-(1,3-Dioxan-2-yl)-1-(4-fluorophenyl)propan-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of 4-fluoro-N-methoxy-N-methylbenzamide (0.94 mmol; 173 mg) in anhydrous THF (2 mL), at −78° C. under argon, was added a solution of (1,3-dioxan-2-ylethyl)magnesium bromide, 0.5M in THF (1.04 mmol; 2.1 mL). The reaction was stirred 16 hours at room temperature. The mixture was cooled to −78° C. and (1,3-dioxan-2-ylethyl)magnesium bromide, 0.5M in THF (2.00 mmol; 4 mL) was added again. The reaction was stirred overnight at room temperature. The mixture was treated with saturated NH4Cl and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, and concentrated in vacuo. The title compound was prepared in quantitative yield, used without further purification.

후처리

  1. temperatureThe mixture was cooled to −78° C.
  2. stirringThe reaction was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customused without further purification

출처 및 근거

ORD 기록
ord-c4a88485f0464179beddef2cb0c55507
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309179B2

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