Potassium Hydroxide → HCID 21249533, compound

HRID 1531600Notes

Reaction equation

HRID 1531600 reaction equation
[CH3:1][C:2]1(C(OCC)=O)[C:16](=[O:17])[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3]1.[OH-].[K+]>C(O)C>[CH3:1][CH:2]1[CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][C:16]1=[O:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 131722424HCID 131722424, compound

Product 1

HCID 21249533HCID 21249533, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-methyl-15-oxocyclopentadeca-3E,11E-dienecarboxylate (0.180 g, 0.59 mmole) and potassium hydroxide (0.15 g, 2.68 mmole) in 50% aqueous ethanol (3 ml) was heated to 65° C. for 5 hours. The solvents were removed by reduced pressure distillation and to the residue was added 5% aqueous hydrochloric acid and methylene chloride. The mixture was shaken, the layers separated, and the organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give the crude product. The crude product was purified by flash chromatography to give 2-methylcyclopentadeca-4E,12E-diene-1-one (0.060 g, 44% yield). C16H26O (234 g/mol): 1HNMR (500 MHz, CDCl3): 1.05 (d, 3H), 1.17 (m, 3H), 1.25-1.41 (m, 3H), 1.97 (m, 4H), 2.08 (m, 2H), 2.27 (m, 1H), 2.36 (m, 1H), 2.46 (m, 1H), 2.52 (m, 1H), 2.59 (m, 1H), 5.32 (m, 3H), 5.46 (m, 1H) ppm. 13CNMR (125 MHz, CDCl3): 17.59, 26.07, 26.72, 27.19, 27.65, 28.74, 30.76, 30.98, 36.59, 42.32, 46.34, 127.81, 129.61, 131.06, 132.12, 213.70 ppm. IR (νmax(cm−1)): 3030(w), 2920(s), 2852(s), 1714(s), 1456(m), 1436(m), 970(s). MS (m/z): 234(M), 219, 191, 177, 163, 149, 135, 121, 109, 95, 81, 67, 55, 41.

Workup

  1. customThe solvents were removed by reduced pressure distillation and to the residue
  2. additionwas added 5% aqueous hydrochloric acid and methylene chloride
  3. customthe layers separated
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude product
  8. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-526b8bfa6a284fe1922e78a5d9516f32
Source dataset
uspto-grants-2001_03
Patent number
US06200254B1

Reaction notes

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