1,4-Dioxaspiro(4.5)decane-8-carbaldehyde → HCID 58562564, compound

HRID 2175493Notes

Reaction equation

HRID 2175493 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH:13]([Mg]Br)([CH3:15])[CH3:14]>C1COCC1>[CH3:14][CH:13]([CH3:15])[CH:11]([CH:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1)[OH:12]

Participants

4

Reactant 2

HCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehydeHCID 178418365HCID 178418365, compound

Product 1

HCID 58562564HCID 58562564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1,4-dioxaspiro[4.5]decane-8-carbaldehyde (693 mg, 4.07 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292) in THF (20 mL) cooled to −78° C. under argon was added a isopropylmagnesium bromide (6 mL, 12 mmol, 1 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/DCM) 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/DCM)
  7. customto afford the product

Sources & evidence

ORD record
ord-7a2f3f1b24cb457c95c19c31aa97e2a3
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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