Ammonium Chloride → cyclohexyl[2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophen-3-yl]methanol

HRID 1877210

반응식

HRID 1877210 반응식
[CH2:1]([C:3]1[S:4][C:5]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2].[CH:16]1([Mg]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:16]1([CH:8]([C:7]2[CH:6]=[C:5]([CH:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[S:4][C:3]=2[CH2:1][CH3:2])[OH:9])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 866463922-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carbaldehydeHCID 178420632HCID 178420632, 화합물

생성물 1

HCID 68511979cyclohexyl[2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophen-3-yl]methanol수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-ethyl-5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carbaldehyde (692 mg) synthesized above in tetrahydrofuran (10 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (4.64 mL) at 0° C., and the mixture was stirred for 2 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, tetrahydrofuran was evaporated using evaporator, and the 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 (ethyl acetate:hexane=3:7, volume ratio) to give the title compound (737 mg, 77%) as a white solid.

후처리

  1. customto quench
  2. customthe reaction, tetrahydrofuran
  3. customwas evaporated
  4. customevaporator
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7, volume ratio)

출처 및 근거

ORD 기록
ord-459ea2d96f5d4f3d8bd0037f62e16176
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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