Dimethylformamide → HCID 86653798, compound

HRID 85172Notes

Reaction equation

HRID 85172 reaction equation
[Li]CCCC.Br[C:7]1[CH:21]=[CH:20][C:10]([O:11][CH2:12][C@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)=[CH:9][C:8]=1[C:22]([F:25])([F:24])[F:23].CN([CH:29]=[O:30])C>C1COCC1>[CH3:18][C:15]1([CH3:19])[O:14][C@@H:13]([CH2:12][O:11][C:10]2[CH:20]=[CH:21][C:7]([CH:29]=[O:30])=[C:8]([C:22]([F:25])([F:24])[F:23])[CH:9]=2)[CH2:17][O:16]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 58278769(S)-4-((4-bromo-3-(trifluoromethyl)phenoxy)methyl)-2,2-dimethyl-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 86653798HCID 86653798, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of nBuLi in hexanes (6.76 mL, 1.6 M in hexanes) was added dropwise to a solution of (S)-4-((4-bromo-3-(trifluoromethyl)phenoxy)methyl)-2,2-dimethyl-1,3-dioxolane (127; 3.20 g, 9 mmol) in THF (50 mL) at −78° C. over a period of 30 min. After stirring for additional 10 min, DMF (1.4 mL) was added dropwise over a period of 10 min. The resulting reaction mixture was warmed to room temperature and stirred for 30 min. It was then quenched with water and extracted by EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:EtOAc=50:1) to afford (S)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-2-(trifluoromethyl)benzaldehyde 128 (2.3 g, 84%).

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred for 30 min
  3. customIt was then quenched with water
  4. extractionextracted by EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography (petroleum ether:EtOAc=50:1)

Sources & evidence

ORD record
ord-d6d5617c58bb49a4a15b2fb913aa7649
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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