Reaction #493189

Reaction equation

LiHMDS

1,4-dioxa-spiro[4.5]decan-8-ol

2,4-difluor-1-nitro-benzene

→

8-(5-Fluoro-2-nitro-phenoxy)-1,4-dioxa-spiro[4.5]decane

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONthan added over 5 min
2. 2
   workup.STIRRINGstirred for 16 h
3. 3
   OtherThe reaction was quenched with sat. ammonium chloride solution
4. 4
   OtherThe solvent was removed under vacuum
5. 5
   OtherThe organic layer was separated
6. 6
   Washthe aqueous phase washed with EtOAc (2×50 ml)
7. 7
   WashThe combined organic phases were washed with brine (50 ml)
8. 8
   Otherseparated
9. 9
   OtherThe organic phase was evaporated
10. 10
    Otherto give a solid that
11. 11
    Otherwas used without further purification

Procedure

63 ml LiHMDS (1 M in THF) were added dropwise to a stirred solution of 10 g 1,4-dioxa-spiro[4.5]decan-8-ol in THF (60 ml) at 0° C. and the reaction stirred for 30 min. A solution of 2,4-difluor-1-nitro-benzene in THF (20 ml) was than added over 5 min and the reaction warmed to rt and stirred for 16 h. The reaction was quenched with sat. ammonium chloride solution and adjusted to pH 7 with 2N HCl. The solvent was removed under vacuum and the residue portioned between EtOAc (200 ml) and water (100 ml). The organic layer was separated and the aqueous phase washed with EtOAc (2×50 ml). The combined organic phases were washed with brine (50 ml) and separated. The organic phase was evaporated to give a solid that was used without further purification.

Source