1,4-Dioxaspiro(4.5)decane-8-carbaldehyde → HCID 58562775, compound

HRID 1896809Notes

Reaction equation

HRID 1896809 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]1([Mg]Br)[CH2:15][CH2:14]1>>[CH:13]1([CH:11]([CH:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[OH:12])[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 98989471,4-Dioxaspiro(4.5)decane-8-carbaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 58562775HCID 58562775, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of 1,4-dioxaspiro[4.5]decane-8-carbaldehyde (1.135 g, 6.668 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 cyclopropylmagnesium bromide (40 mL, 20 mmol, 0.5 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% ethyl acetate/heptane) 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% ethyl acetate/heptane)
  7. customto afford the product

Sources & evidence

ORD record
ord-98085859b683426f8449205d351bd830
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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