Water → Cyclohexyl[5-(1,3-dioxolan-2-yl)-2-ethylthiophen-3-yl]methanol

HRID 1877256Notes

Reaction equation

HRID 1877256 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[S:10][C:9]([CH2:11][CH3:12])=[C:8]([CH:13]=[O:14])[CH:7]=1.[CH:15]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.O1CCCC1.O>O1CCCC1>[CH:15]1([CH:13]([C:8]2[CH:7]=[C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)[S:10][C:9]=2[CH2:11][CH3:12])[OH:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 866463965-(1,3-Dioxolan-2-yl)-2-ethylthiophene-3-carbaldehydeHCID 178420632HCID 178420632, compound

Product 1

HCID 68515315Cyclohexyl[5-(1,3-dioxolan-2-yl)-2-ethylthiophen-3-yl]methanolYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(1,3-dioxolan-2-yl)-2-ethylthiophene-3-carbaldehyde (6.36 g) synthesized above in tetrahydrofuran (130 mL) was added dropwise 1.0M cyclohexylmagnesium bromide-tetrahydrofuran solution (40 mL) at 0° C., and the mixture was stirred for 1.5 hr under an argon atmosphere. Water 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 (30% ethyl acetate/hexane) to give the title compound (6.30 g, 71%) as a pale-yellow oil.

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 (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bc5f6c9cd2aa42eca4245a80403ec1d4
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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