Iodine → 8-(But-3-en-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 2380402Notes

Reaction equation

HRID 2380402 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[Mg].II.[CH2:9]1[O:19][C:12]2([CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[O:11][CH2:10]1>O1CCCC1.[Cl-].[NH4+]>[CH2:10]1[O:11][C:12]2([CH2:13][CH2:14][C:15]([CH2:5][CH2:4][CH:3]=[CH2:2])([OH:18])[CH2:16][CH2:17]2)[O:19][CH2:9]1

Participants

7

Reactant 4

HCID 807IodineHCID 21241Homoallyl bromideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

Product 1

HCID 542418378-(But-3-en-1-yl)-1,4-dioxaspiro[4.5]decan-8-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a mixture of 4-bromo-1-butene (1.0 g) and magnesium turnings (1.77 g) in dry tetrahydrofuran (10 mL) was added a crystal of iodine and the mixture was stirred at room temperature until complete reaction had occurred. To this mixture was added 1.4-cyclohexanedione monoethylene ketal (780 mg) in tetrahydrofuran (1 mL) at 0° C. After 1 h at 0° C. and 1 h at room temperature the reaction mixture was diluted with ammonium chloride solution and the product was extracted with ether. After drying over magnesium sulfate the solvent was removed in vacuo and the residue was subjected to flash chromatography with 25% ethyl acetate/hexane as the eluent to afford 4-(3-butenyl)-4-hydroxy-cyclohexanone ethylene ketal as an oil.

Workup

  1. extractionthe product was extracted with ether
  2. dry with materialAfter drying over magnesium sulfate the solvent
  3. customwas removed in vacuo

Sources & evidence

ORD record
ord-274243a136ee48c5b767d4b9e609d444
Source dataset
uspto-grants-1994_11
Patent number
US05367077

Reaction notes

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