Sodium Hydroxide → HCID 68723299, compound

HRID 1471375Notes

Reaction equation

HRID 1471375 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH:4][CH3:5].[C:6]1(=[CH:9][C:10](=[O:12])[CH3:11])[CH2:8][CH2:7]1.[OH-].[Na+]>CCOCC.[Cl-].[Cl-].[Zn+2]>[CH3:5][C@@H:4]1[CH:3]=[CH:2][CH2:1][C:6]2([CH2:8][CH2:7]2)[C@@H:9]1[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15301Penta-1,3-dieneHCID 127208261-Cyclopropylidenepropan-2-one

Product 1

HCID 68723299HCID 68723299, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

At 20° C. under N2, a suspension of anhydrous ZnCl2 (0.31 g, 2.29 mmol) in Et2O (1.5 ml) was treated with 1,3-pentadiene (65% pure, 3.34 ml, 22.9 mmol) then with a solution of 1-cyclopropylidenepropan-2-one (0.44 g, 4.58 mmol) in Et2O (1,5 ml). After 24 h stirring, the resulting mixture treated with 6N aq. NaOH (3.1 ml) and the aqueous phase extracted three time with Et2O. The combined organic phases were washed twice with a saturated aqueous solution of NH4Cl, once with a saturated aqueous solution of NaCl, dried (MgSO4), and concentrated. FC (100 g SiO2, pentane/Et2O 10:0.5) of the crude product (1.12 g) gave rel-(4R,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (279 mg, 36%).

Workup

  1. extractionthe aqueous phase extracted three time with Et2O
  2. washThe combined organic phases were washed twice with a saturated aqueous solution of NH4Cl, once with a saturated aqueous solution of NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3021bfc9331844d39de5ceed0acf5cb3
Source dataset
uspto-grants-2015_04
Patent number
US09012391B2

Reaction notes

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