Hydrochloric Acid → HCID 13693403, compound

HRID 846235Notes

Reaction equation

HRID 846235 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].Cl>C1COCC1.O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH:10]([CH3:11])[CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 60984Methyl bromoacetateHCID 8211711-[4-(Methylthio)phenyl]-1-propanoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 13693403HCID 13693403, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The ketone from Step A (180 mg) in THF (2 ml) was added to a solution of lithium diisopropylamide (1.1 mmole) in THF (3 ml) at -78° under N2 atmosphere. After 15 minutes methyl bromoacetate (100 μl) was added and the mixture was warmed to ambient temperature and stirred 12 hours. The mixture was poured into water (15 ml) and conc. HCl (2 ml), extracted with CH2Cl2 and the extracts were dried (Na2SO4) evaporated to dryness and the residue purified by chromatography on silica gel to provide the title compound as an oil. NMR (CDCl3): 1.2 (3H, d), 2.55 (3H, s), 2.3-3.1 (2H, m), 3.65 (3H, s), 3.95 (1H, m), 7.3 (2H, d), 7.95 (2H, d).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialthe extracts were dried (Na2SO4)
  3. customevaporated to dryness
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d453165e87fb4a34877f3cb13e11244f
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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