1,4-Dioxaspiro(4.5)decane-8-carbaldehyde → HCID 58562619, compound

HRID 1896806Notes

Reaction equation

HRID 1896806 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.[CH2:13]([Mg]Br)[CH:14]=[CH2:15]>>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([OH:12])[CH2:15][CH:14]=[CH2:13])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 58562619HCID 58562619, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of 1,4-dioxaspiro[4.5]decane-8-carbaldehyde (627 mg, 3.68 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292) cooled to −78° C. under argon was added a allylmagnesium bromide (5 mL, 5 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-e67a63e256614ff6bc8ab767a9ea9434
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…