Cyclohexanone → 1-Benzylcyclohexan-1-ol

HRID 1180732Notes

Reaction equation

HRID 1180732 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([Mg]Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1.C(OCC)C>[CH2:8]([C:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 178418336HCID 178418336, compound

Product 1

HCID 747531-Benzylcyclohexan-1-olYield 66%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3.00 g (30.57 mmol) of cyclohexanone in 102 mL of tetrahydrofuran at 0° C. was added 36.68 mL (36.68 mmol) of a 1 M solution of benzyl magnesium chloride in diethyl ether and the mixture was allowed to warm to RT and stirred for 17 h. The reaction was quenched with methanol, followed by water. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give 3.84 g (66%) of 1-benzylcyclohexanol. Then, 2.23 g (11.69 mmol) of the compound was dissolved in 5.8 mL of toluene and 2.00 g (11.69 mmol) of methyl(2S)-2-isocyanatohexanoate was added. The mixture was heated at 85° C. for 12 d. The solution was concentrated and the residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (1:6) to give 1.90 g (45%) of methyl(2S)-2-({[(1-benzylcyclohexyl)oxy]carbonyl}amino)hexanoate. Rf=0.39 (1:4 ethyl acetate:hexanes); 1H NMR (300 MHz, DMSO-d6) δ 7.36 (d, J=8 Hz, 1H), 7.25-7.10 (m, 5H), 4.02-3.97 (m, 1H), 3.65 (s, 3H), 3.12 (s, 2H), 1.72-1.06 (m, 16H), 0.87 (t, J=7 Hz, 3H).

Workup

  1. customThe reaction was quenched with methanol
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5cdc3ba294b84db9a12fa6a16ea531c7
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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