Citric Acid → HCID 59331237, compound

HRID 1881864Notes

Reaction equation

HRID 1881864 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]2[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]2)[N:6]=1.CCCCCC.C([Li])CCC.CN(C)[CH:27]=[O:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH3:12][C:9]1([CH3:13])[O:8][CH:7]([C:5]2[N:6]=[C:2]([CH:27]=[O:28])[S:3][CH:4]=2)[CH2:11][O:10]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6228DimethylformamideHCID 59331272HCID 59331272, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 59331237HCID 59331237, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 2-bromo-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-thiazole (3.00 g) in tetrahydrofuran (40 mL) was slowly added a 1.6M n-butyllithium hexane solution (7.8 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 1 hr, and N,N-dimethylformamide (2.50 g) was added. The reaction mixture was warmed to room temperature, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (1.03 g, yield 42%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:5, volume ratio).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ece59b52b32f44a6adfd9d0b481cddee
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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