1,4-Dioxaspiro(4.5)decane-8-carbaldehyde → 1-(1,4-Dioxaspiro[4.5]decan-8-yl)prop-2-en-1-ol

HRID 1896812Notes

Reaction equation

HRID 1896812 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)=[CH2:14]>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([OH:12])[CH:13]=[CH2:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 585627571-(1,4-Dioxaspiro[4.5]decan-8-yl)prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1,4-dioxaspiro[4.5]decane-8-carbaldehyde (860 mg, 5.05 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292) in THF (6 mL) cooled to −78° C. under argon was added a vinylmagnesium bromide (20 mL, 20 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/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-527446dabf30411ea0d963fc9a4e2b58
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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