Ammonium Chloride → 2-[Cyclohexyl(hydroxy)methyl]-3-methyl-1-benzofuran-5-carbonitrile

HRID 2091155노트

반응식

HRID 2091155 반응식
[CH:1]([C:3]1[O:4][C:5]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:6]=2[C:7]=1[CH3:8])=[O:2].[CH:15]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[Cl-].[NH4+]>O1CCCC1>[CH:15]1([CH:1]([OH:2])[C:3]2[O:4][C:5]3[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][C:6]=3[C:7]=2[CH3:8])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 824063072-Formyl-3-methyl-1-benzofuran-5-carbonitrileHCID 178419651HCID 178419651, 화합물

생성물 1

HCID 667770382-[Cyclohexyl(hydroxy)methyl]-3-methyl-1-benzofuran-5-carbonitrile수율 43%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution (30 mL) of 2-formyl-3-methyl-1-benzofuran-5-carbonitrile (1.49 g) synthesized above in tetrahydrofuran was added a 1.0M solution (12.1 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, and the reaction mixture 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 (25% ethyl acetate/hexane), and then purified by NH silica gel column chromatography (ethyl acetate) to give the title object compound (922 mg, 43%) as a pale-yellow solid.

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (25% ethyl acetate/hexane)
  8. custompurified by NH silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-ba5c5796d4f24dc5a5f8042e1626eddd
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

반응 노트

불러오는 중…