Trifluoroacetic acid → HCID 118021506, compound

HRID 575835Notes

Reaction equation

HRID 575835 reaction equation
[Br:1][C:2]1[C:10]2[O:9][C:8]([CH:11]3[CH2:13][CH2:12]3)=[CH:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>[OH-].[Na+]>[Br:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]3[CH2:13][CH2:12]3)[CH2:7][C:6]=2[CH:5]=[C:4]([S:14]([CH3:17])(=[O:15])=[O:16])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118021660HCID 118021660, compound

Product 1

HCID 118021506HCID 118021506, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of the title compound from Step 1 (250 mg, 0.79 mmol) in Et3SiH (516 mg, 4.44 mmol) at 0° C. was added TFA (5.43 g, 47.59 mmol) in one portion. The reaction mixture was warmed up to rt and stirred for 48 hours. Aqueous NaOH solution (10 mL, 1 N) was added slowly to the above solution. The mixture was extracted with EtOAc (10 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (PE to PE/EA=2/1) to give the title compound (83 mg, 33%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.90 (s, 1H), 7.64 (s, 1H), 4.47-4.43 (m, 1H), 3.51-3.47 (m, 1H), 3.23-3.17 (m, 1H), 3.04 (s, 3H), 1.24-1.22 (m, 1H), 0.74-0.55 (m, 3H), 0.44-0.41 (m, 1H).

Workup

  1. extractionThe mixture was extracted with EtOAc (10 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (PE to PE/EA=2/1)

Sources & evidence

ORD record
ord-f17b9e4686b84f6f8b83df267dd177c0
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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