Tetrahydrofuran → HCID 58562785, compound

HRID 1896846Notes

Reaction equation

HRID 1896846 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]Cl)[CH3:17].[CH2:20]1COC[CH2:21]1>>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([C:11]([OH:13])([CH2:16][CH3:17])[CH2:20][CH3:21])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateHCID 178461633HCID 178461633, compound

Product 1

HCID 58562785HCID 58562785, compound

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate (0.754 g, 3.52 mmol, prepared as described in Pearson, et al. in J. Org. Chem. 1997, 62(16), 5284-5292) in THF (20 mL) cooled to −78° C. under argon was added a ethylmagnesium chloride (9 mL, 18 mmol, 2 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-df78312a6aed486bb7b706fed891c3fc
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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