1,4-Dioxaspiro[4.5]decan-8-one → HCID 58456119, compound

HRID 2175534Notes

Reaction equation

HRID 2175534 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH:12]([Mg]Cl)([CH3:14])[CH3:13]>C1COCC1>[CH:12]([C:8]1([OH:11])[CH2:7][CH2:6][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:10][CH2:9]1)([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418918HCID 178418918, compound

Product 1

HCID 58456119HCID 58456119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of commercially available 1,4-dioxaspiro[4.5]decan-8-one (3.00 g, 19.2 mmol, in THF (20 mL) cooled to −78° C. under argon was added a isopropylmagnesium chloride (10 mL, 20 mmol, 2 M in THF) dropwise. After the complete addition, the reaction mixture was allowed to reach room temperature overnight. It was then re-cooled to −78° C. and quenched with saturated NaHCO3 solution and warmed to room temperature. After extraction with ether, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, 0-100% ether/hexanes) to afford the product.

Workup

  1. additionAfter the complete addition
  2. customquenched with saturated NaHCO3 solution
  3. temperaturewarmed to room temperature
  4. extractionAfter extraction with ether
  5. concentrationthe organic layer was concentrated in vacuo
  6. customthe residue purified by flash chromatography (silica gel, 0-100% ether/hexanes)
  7. customto afford the product

Sources & evidence

ORD record
ord-24efe9f394ed4fc495802355d0c54fd7
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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