Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate → HCID 58562619, compound

HRID 1896844Notes

Reaction equation

HRID 1896844 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]([O:13]CC)=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH2:16]([Mg]Br)[CH:17]=[CH2:18]>C1COCC1>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([CH:11]([OH:13])[CH2:18][CH:17]=[CH2:16])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateHCID 178455850HCID 178455850, compound

Product 1

HCID 58562619HCID 58562619, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (1.12 g, 5.24 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292) in THF (10 mL) cooled to −78° C. under argon was added a allylmagnesium bromide (18 mL, 18 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-6692c82d24d04687aa5350c14169b9e7
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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