Dimethylformamide → HCID 86642144, compound

HRID 1024114Notes

Reaction equation

HRID 1024114 reaction equation
C([Li])CCC.[C:6]([Si:10]([CH3:38])([CH3:37])[O:11][C@H:12]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C@@H:28]([CH2:29][CH2:30][CH2:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[CH2:27][CH2:26][CH:25]=2)=[CH:20][CH:19]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH3:9])([CH3:8])[CH3:7].CN([CH:42]=[O:43])C>CCOCC>[C:6]([Si:10]([CH3:38])([CH3:37])[O:11][C@H:12]([C:18]1[CH:19]=[CH:20][C:21]([C:24]2[C@@H:28]([CH2:29][CH2:30][CH2:31][C:32]3[S:33][C:34]([CH:42]=[O:43])=[CH:35][CH:36]=3)[CH2:27][CH2:26][CH:25]=2)=[CH:22][CH:23]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68705485HCID 68705485, compoundHCID 178418339Butyllithium

Product 1

HCID 86642144HCID 86642144, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

n-Butyllithium (0.14 mL, 0.22 mmol, 1.6 M/hexanes) was added to an ice cold solution of 41 (53 mg, 0.11 mmol) in 0.5 mL ether. After 1 h, DMF (85 μL, 1.1 mmol) was added and the reaction was allowed to stir for 40 min. At this time, the reaction was quenched by addition of 10 mL saturated NH4Cl solution. The mixture was extracted with ethyl acetate (2×20 mL) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography using a Combiflash unit by Teledyne Isco (12 g silica gel, 0%→15% ethyl acetate/hexanes) which gave the title compound (43 mg, 0.084 mmol, 77%).

Workup

  1. customAt this time, the reaction was quenched by addition of 10 mL saturated NH4Cl solution
  2. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
  3. dry with materialthe combined ethyl acetate solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f38312c39cfd4b719b155ea714bd9ff5
Source dataset
uspto-grants-2014_05
Patent number
US08722726B2

Reaction notes

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