Chloroacetone → HCID 71076611, compound

HRID 1774489Notes

Reaction equation

HRID 1774489 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][Si](C(C)C)(C(C)C)C(C)C)[CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl[CH2:41][C:42](=[O:44])[CH3:43].CCN(C(C)C)C(C)C>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH2:41][C:42](=[O:44])[CH3:43])[CH:5]=1

Participants

7

Reactant 4

HCID 6571Chloroacetone2×HCID 81531Diisopropylethylamine2×HCID 2724141Tetrabutylammonium FluorideHCID 71076616HCID 71076616, compound

Product 1

HCID 71076611HCID 71076611, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Triisopropylsilanylsulfanyl-isonicotinic acid methyl ester (1.5 g, 4.6 mmol) was dissolved in THF (50 mL) and tetrabutylammonium fluoride (1 M in THF, 6.9 mL, 6.9 mmol) was added. After 15 minutes TLC indicated complete cleavage of the protecting group and chloroacetone (0.440 mL, 5.52 mmol) and Hünig's base (2.8 mL, 16.1 mmol) were added. After 1 hour additional portions of chloroacetone (1.2 eq.) and Hünig's base (3.5 eq.) were added. After stirring at room temperature for 2 hours the reaction was diluted with EtOAc and washed with H2O/brine with back-extraction. The combined organic portions were dried over MgSO4 and concentrated then purified on silica gel (0-100% EtOAc in hexanes) to yield the title compound.

Workup

  1. washwashed with H2O/brine with back-extraction
  2. dry with materialThe combined organic portions were dried over MgSO4
  3. concentrationconcentrated
  4. customthen purified on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-658e2781aada4ba984ac2ed41984a35d
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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