Trimethylsilane → (9-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-8-yloxy)trimethylsilane

HRID 1803209Notes

Reaction equation

HRID 1803209 reaction equation
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:25](=[O:26])[CH2:24][CH2:23][C:18]3([O:22][CH2:21][CH2:20][O:19]3)[CH2:17]2)=[CH:12][CH:11]=1.[CH3:27][SiH:28]([CH3:30])[CH3:29]>C1COCC1.CCOC(C)=O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:17][C:18]3([O:19][CH2:20][CH2:21][O:22]3)[CH2:23][CH:24]=[C:25]2[O:26][Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 70435TrimethylsilaneHCID 2724682Lithium diisopropylamideHCID 668594007-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-one

Product 1

HCID 66858541(9-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-8-yloxy)trimethylsilaneYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step AAC (1): Followed a method described by A. de Meijer et. al Chem. Eur. J. 2007, 13, 3739. Lithium diisopropylamide (1.8 M in THF, 1.26 mL, 2.26 mmol) was added to a −78° C. solution of 7-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-one (515 mg, 2.06 mmol, O. Dirat et. al Tetrahedron Lett. 2006, 47, 1295) in THF (7 mL). The resulting mixture was allowed to stir for 1 hr. Trimethylsilane (0.289 mL, 2.264 mmol) was added and the mixture was allowed to warm to rt and stir for 30 min. The crude reaction was diluted with EtOAc and washed with saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo to afford (9-(4-fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-8-yloxy)trimethylsilane (696 mg, 100% yield) as a yellow solid. The crude product was used for subsequent chemistry without purification or characterization.

Workup

  1. stirringstir for 30 min
  2. customThe crude reaction
  3. washwashed with saturated sodium bicarbonate solution
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-4cbf0cec6b3643edb81746a2e014a7ca
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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