1,4-Dioxaspiro[4.5]decan-8-one → HCID 59030604, compound

HRID 1045365Notes

Reaction equation

HRID 1045365 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH:12]1([Mg]Br)[CH2:14][CH2:13]1>O1CCCC1>[CH:12]1([C:8]2([OH:11])[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418630HCID 178418630, compound

Product 1

HCID 59030604HCID 59030604, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (2 g, 12.80 mmol) was dissolved in dry tetrahydrofuran (20 mL). The reaction mixture was cooled to −78° C. Cyclopropylmagnesium bromide (51.2 mL, 25.61 mmol) was added dropwise over a period of 10 min. The reaction mixture was stirred for 4 h, quenched with sat. NH4Cl and extracted with ethyl acetate. The solvent was evaporated and the crude product was used without further purification in the next step.

Workup

  1. customquenched with sat. NH4Cl
  2. extractionextracted with ethyl acetate
  3. customThe solvent was evaporated
  4. customthe crude product was used without further purification in the next step

Sources & evidence

ORD record
ord-f43193a934664670be5ac999bbd97168
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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