(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehyde → 1-((1r,2s,5r)-2-Isopropyl-5-methylcyclohexyl)butan-1-ol

HRID 546371Notes

Reaction equation

HRID 546371 reaction equation
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]=[O:12])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[CH2:14][CH3:15]>C1COCC1>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:12])[CH2:13][CH2:14][CH3:15])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11252239(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehydeHCID 178455851HCID 178455851, compound

Product 1

HCID 671905921-((1r,2s,5r)-2-Isopropyl-5-methylcyclohexyl)butan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde (4.64 g, 27.6 mmol) in THF (120 mL) at 0° C. was slowly added propylmagnesium bromide (2 M in THF, 28 mL). After the reaction was allowed to warm to room temperature over 1 h it was again cooled to 0° C. The reaction was quenched with 1 N HCl and partitioned between brine and MTBE. The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica chromatography to give the desired alcohol (1.65 g).

Workup

  1. customat 0° C.
  2. temperaturewas again cooled to 0° C
  3. customThe reaction was quenched with 1 N HCl
  4. custompartitioned between brine and MTBE
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-464c650a19c84d0eb862357d1b3f6469
Source dataset
uspto-grants-2011_05
Patent number
US07935848B2

Reaction notes

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