Carbon Dioxide → HCID 14770853, compound

HRID 1090390Notes

Reaction equation

HRID 1090390 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10]2)=[C:4]([F:18])[CH:3]=1.C([Li])CCC.[C:24](=[O:26])=[O:25]>O1CCCC1>[F:8][C:7]1[CH:6]=[C:5]([CH:9]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10]2)[C:4]([F:18])=[CH:3][C:2]=1[C:24]([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 280Carbon Dioxide2×HCID 14770852HCID 14770852, compoundHCID 178418339Butyllithium

Product 1

HCID 14770853HCID 14770853, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 31.9 g (0.1 mol) of 7-(4-bromo-2,5-difluorophenyl)-1,4-dioxaspiro[4.4]nonane in 300 ml of dry tetrahydrofuran, under an argon atmosphere at -78° C., was treated with 40 ml (0.1 mol) of 2.5 M n-butyl lithium (hexane solution). The solution was warmed to -40° and poured onto 500 g of finely crushed dry ice and the mixture allowed to stand until the dry ice evaporated (18 hours). The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate/1.0 M hydrochloric acid (500 ml ea). The organic layer was washed with water, dried (MgSO4), and evaporated in vacuo to give 18.9 g of the title compound.

Workup

  1. temperatureThe solution was warmed to -40°
  2. customevaporated (18 hours)
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between ethyl acetate/1.0 M hydrochloric acid (500 ml ea)
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cad9b83c38ac46a5a31861eedcde5c4e
Source dataset
uspto-grants-1992_01
Patent number
US05081254

Reaction notes

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