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

HRID 1877210

Reaction equation

HRID 1877210 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-459ea2d96f5d4f3d8bd0037f62e16176
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Linked notes

Loading…