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

HRID 1877223Notes

Reaction equation

HRID 1877223 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([CH:10]2[CH2:15][CH2:14][S: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][S: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 866463932-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophene-3-carbaldehydeHCID 178420632HCID 178420632, compound

Product 1

HCID 68511464cyclohexyl[2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophene-3-carbaldehyde (1.85 g) synthesized above in tetrahydrofuran (20 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (11.6 mL) at 0° C., and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, 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 (20% ethyl acetate/hexane) to give the title compound (1.91 g, 76%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe 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 (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-de52a4438ac14cf389120d1fdca97f1d
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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