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

HRID 2175495Notes

Reaction equation

HRID 2175495 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-230d457b34f045b48f17e96b2c6d0677
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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