Cyclopentanecarbaldehyde → 1-Cyclopentylprop-2-yn-1-ol

HRID 1260579Notes

Reaction equation

HRID 1260579 reaction equation
[CH:1]1([CH:6]=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([Mg]Br)#[CH:9]>O1CCCC1>[CH:1]1([CH:6]([OH:7])[C:8]#[CH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70106CyclopentanecarbaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 210622471-Cyclopentylprop-2-yn-1-olYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.87 ml of cyclopentanecarboxaldehyde (8.15 mmol; Aldrich) in 10 ml of tetrahydrofuran is added to 18 ml of a commercially available 0.5 M solution of ethynylmagnesium bromide in tetrahydrofuran (10 mmol, Aldrich) cooled beforehand to 0° C. The mixture is then stirred for 2 hours at ambient temperature and a saturated solution of NH4Claq is added. The mixture is extracted with ethyl acetate and the organic phases are then combined, washed with a saturated solution of NaClaq, dried over sodium sulphate, filtered, and concentrated under vacuum. 0.931 g of (±)-1-cyclopentylprop-2-yn-1-ol is obtained in the form of a light brown oil with a yield of 92%.

Workup

  1. temperaturecooled
  2. custombeforehand to 0° C
  3. additiona saturated solution of NH4Claq is added
  4. extractionThe mixture is extracted with ethyl acetate
  5. washwashed with a saturated solution of NaClaq
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c3aba6cdef4e4f3c934d7c4ee668da43
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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