Trifluoroacetic acid → HCID 15284123, compound

HRID 1609122Notes

Reaction equation

HRID 1609122 reaction equation
[C:1]([O:4]C(C)(C)C)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24]([CH2:30][C:31]1[C:36](=[O:37])[CH2:35][CH2:34][CH2:33][C:32]=1OS(C(F)(F)F)(=O)=O)=[CH:25]2.FC(F)(F)C(O)=O>C1COCC1.C(Cl)Cl>[Br:19][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24]([CH2:30][C:31]1[C:36](=[O:37])[CH2:35][CH2:34][CH2:33][C:32]=1[CH2:2][C:1]([OH:4])=[O:3])=[CH:25]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10908tert-Butyl acetateHCID 2733832Lithium HexamethyldisilazideHCID 15284122HCID 15284122, compound

Product 1

HCID 15284123HCID 15284123, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In to a cold (-78° C.) solution of tert-butyl acetate (2.7 mL, 19.96 mmol) in THF (35 mL) was added lithium bis(trimethylsilyl)amide solution (1.0M, 21.62 mL, 21.62 mmol). After stirring for 2 hours a solution of trifluoromethanesulfonic acid 2-(5-bromo-naphthalen-2-ylmethyl)-3-oxo-cyclohex-1-enyl ester (7.7 g, 16.63 mmol) in THF (15 mL) was added dropwise. The mixture was stirred for 1 hour, quenched with aqueous NH4Cl, poured in to H2O and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation gave a yellow oil residue which was taken up in methylene chloride (100 mL) and treated with trifluoroacetic acid (10 mL). The mixture was stirred for 5 hours and then the volatiles were removed in vacuo. The residue was purified by flash chromatography on acidic silica gel (eluting solvent hexane/EtOAc 1/1) to give a yellow solid (4.1 g, 66% yield, m.p 56°-58° C.).

Workup

  1. additionwas added dropwise
  2. customquenched with aqueous NH4Cl
  3. additionpoured in to H2O
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried over MgSO4
  6. customEvaporation
  7. customgave a yellow oil residue which
  8. stirringThe mixture was stirred for 5 hours
  9. customthe volatiles were removed in vacuo
  10. customThe residue was purified by flash chromatography on acidic silica gel (eluting solvent hexane/EtOAc 1/1)
  11. customto give a yellow solid (4.1 g, 66% yield, m.p 56°-58° C.)

Sources & evidence

ORD record
ord-1576916f043442a481ae7a1ed6bb7f79
Source dataset
uspto-grants-1995_03
Patent number
US05399588

Reaction notes

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