4-(Hydroxymethyl)cyclohexan-1-one → HCID 23263401, compound

HRID 707031Notes

Reaction equation

HRID 707031 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[CH3:10][Mg]Cl>O1CCCC1>[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][C:6]([CH3:10])([OH:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 128928674-(Hydroxymethyl)cyclohexan-1-oneHCID 178418332HCID 178418332, compound

Product 1

HCID 23263401HCID 23263401, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-(Hydroxymethyl)cyclohexanone (800 mg) in tetrahydrofuran (15 mL) was treated with 3 M methylmagnesium chloride in tetrahydrofuran (6.24 mL) at 0° C. The reaction was warmed to room temperature over 2 hours and quenched with methanol and water. The resulting mixture was concentrated and the residue was suspended in ethyl acetate. The precipitates were filtered off and the filtrate was concentrated. The residue was purified by chromatography, eluting with 0-100% ethyl acetate in hexane to provide the title compound.

Workup

  1. customquenched with methanol and water
  2. concentrationThe resulting mixture was concentrated
  3. filtrationThe precipitates were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography
  6. washeluting with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-05d6fbe01a17439990c7a2c4e15a95e7
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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