Acetylene → 6-Cyclopentylidene-3-methylhex-1-yn-3-ol

HRID 2185162Notes

Reaction equation

HRID 2185162 reaction equation
[CH:1]#C.[C:3]([O:7][K])([CH3:6])([CH3:5])[CH3:4].[C:9]1(=[CH:14][CH2:15]CC(=O)C)[CH2:13][CH2:12][CH2:11][CH2:10]1>C1COCC1>[C:9]1(=[CH:14][CH2:15][CH2:4][C:3]([CH3:6])([OH:7])[C:5]#[CH:1])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6326AcetyleneHCID 135280135-Cyclopentylidenepentan-2-oneHCID 178418922HCID 178418922, compound

Product 1

HCID 184338526-Cyclopentylidene-3-methylhex-1-yn-3-olYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetylene was bubbled for 50 minutes through a solution of tBuOK (33.8 g; 0.30 mol) in THF (240 ml) at 0° C. The resulting beige suspension was treated with 5-cyclopentylidenepentan-2-one (41.7 g; 0.27 mol) added dropwise for 15 minutes at 0° C. The resulting mixture was warmed gently to room temperature and quenched with saturated NH4Cl (180 ml). The aqueous phase was separated and extracted with MTBE (2×120 ml). The combined organic layers were washed with H2O (240 ml), brine (100 ml), dried over MgSO4, and concentrated in vacuo. Distillation (69° C.-71° C./0.09 torr) afforded 38.95 g (81% yield) of 6-cyclopentylidene-3-methylhex-1-yn-3-ol.

Workup

  1. additionadded dropwise for 15 minutes at 0° C
  2. customquenched with saturated NH4Cl (180 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted with MTBE (2×120 ml)
  5. washThe combined organic layers were washed with H2O (240 ml), brine (100 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. distillationDistillation (69° C.-71° C./0.09 torr)

Sources & evidence

ORD record
ord-d457b3ff82a24073bb695f55caf34eed
Source dataset
uspto-grants-2002_06
Patent number
US06399811B1

Reaction notes

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