(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehyde → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol

HRID 546373Notes

Reaction equation

HRID 546373 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)[C:14]#[CH: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])[CH2:15][C:14]#[CH:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11252239(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehydeHCID 178455849HCID 178455849, compound2×

Product 1

HCID 866439371-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-olYield 37.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde (1.0 g, 6.0 mmol) in THF (10 mL) at 0° C. was slowly added propargyl magnesium bromide (1 M, 8.9 mmol). After the reaction was allowed to warm to room temperature overnight 1.5 equivalents of additional propargyl magnesium bromide were added and the reaction was allowed to stir for 6 additional h. The reaction was again cooled to 0° C. and then 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 (0.47 g).

Workup

  1. customat 0° C.
  2. additionwere added
  3. customquenched 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-345f706e4ffc4137be4f291a604843b2
Source dataset
uspto-grants-2011_05
Patent number
US07935848B2

Reaction notes

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