4-(Hydroxymethyl)cyclohexan-1-one → HCID 67226336, compound

HRID 2045099Notes

Reaction equation

HRID 2045099 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH2:10]([Mg]Br)[CH3:11]>O1CCCC1>[CH2:10]([C:6]1([OH:9])[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]1)[CH3:11]

Participants

4

Reactant 2

HCID 128928674-(Hydroxymethyl)cyclohexan-1-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 67226336HCID 67226336, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Hydroxymethyl)cyclohexanone (1.22 g) in tetrahydrofuran (20 mL) was treated with 1M ethylmagnesium bromide in tetrahydrofuran (28.6 mL) at 0° C. The reaction was warmed to room temperature over 4 hours and quenched with methanol (2 mL) and water (2 mL). The resulting mixture was concentrated and the residue was suspended in ethyl acetate. The precipitates were filtered off and the filtrate was concentrated and purified by flash chromatography, eluted with 0-100% ethyl acetate in hexane to provide the title compound.

Workup

  1. customquenched with methanol (2 mL) and water (2 mL)
  2. concentrationThe resulting mixture was concentrated
  3. filtrationThe precipitates were filtered off
  4. concentrationthe filtrate was concentrated
  5. custompurified by flash chromatography
  6. washeluted with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0d2e73c6b6df4b7098e0fd7fa8cf4de5
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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