Ammonium Chloride → Cyclohexyl(6-fluoro-3-methyl-1-benzofuran-2-yl)methanol

HRID 2091145노트

반응식

HRID 2091145 반응식
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH3:11])=[C:7]([CH:9]=[O:10])[O:8][C:4]=2[CH:3]=1.[CH:14]1([Mg]Br)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+]>O1CCCC1>[CH:14]1([CH:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([F:1])[CH:13]=[CH:12][C:5]=3[C:6]=2[CH3:11])[OH:10])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 823743336-Fluoro-3-methyl-1-benzofuran-2-carbaldehydeHCID 178419651HCID 178419651, 화합물

생성물 1

HCID 66778852Cyclohexyl(6-fluoro-3-methyl-1-benzofuran-2-yl)methanol수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution (20 mL) of 6-fluoro-3-methyl-1-benzofuran-2-carbaldehyde (940 mg) synthesized above in tetrahydrofuran was added a 1.0M solution (7.92 mL) of cyclohexylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, tetrahydrofuran was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane) to give the title object compound (931 mg, 67%) as a pale-yellow oil.

후처리

  1. customto quench
  2. customthe reaction, tetrahydrofuran
  3. customwas evaporated in an evaporator
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-7c15a985818a4855bbbc36f722a39a1d
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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