Sodium hydride → HCID 58495519, compound

HRID 1191109Notes

Reaction equation

HRID 1191109 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][SH:4].[H-].[Na+].[C:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15](=[O:18])[CH2:16]Br)=[CH:13][CH:12]=1)#[N:10]>C1COCC1>[F:1][C:2]([F:6])([F:5])[CH2:3][S:4][CH2:16][C:15]([C:14]1[CH:19]=[CH:20][C:11]([C:9]#[N:10])=[CH:12][CH:13]=1)=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 986544-(Bromoacetyl)benzonitrileHCID 41339242,2,2-Trifluoroethanethiol

Product 1

HCID 58495519HCID 58495519, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,2-trifluoroethanethiol (1.5 mL, 17.2 mmol) in anhydrous THF (28 mL) at 0° C. under nitrogen, add sodium hydride (629 mg, 15.7 mmol) and stir for 15 min. Then, add 4-cyanophenacyl bromide (3.2 g, 14.3 mmol) and stir at ambient temperature overnight. Quench with water and extract with EtOAc. Dry the combined organics extracts over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (7:3) to obtain the desired intermediate (3.1 mg, 84%).

Workup

  1. stirringstir at ambient temperature overnight
  2. customQuench with water
  3. extractionextract with EtOAc
  4. customDry the combined
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (7:3)

Sources & evidence

ORD record
ord-c071cac56c134fb59b1c86218108c29a
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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