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

HRID 1520690Notes

Reaction equation

HRID 1520690 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-d04dec9692ec43a885d04c93230385bc
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

Loading…