Sulfuric Acid → HCID 54682555, compound

HRID 1445949Notes

Reaction equation

HRID 1445949 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:26])[O:10]/[C:11](=[CH:15]\[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)/[C:12]=2[O:13]C)=[CH:4][CH:3]=1.[Li+].[Br-].OS(O)(=O)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:26])[O:10]/[C:11](=[CH:15]\[C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)/[C:12]=2[OH:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 82050Lithium BromideHCID 57567190HCID 57567190, compound

Product 1

HCID 54682555HCID 54682555, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A stirred mixture of 3-(4-chlorophenyl)-4-methoxy-5-[(Z)-1-naphthylmethyl-idene]furan-2(5H)-one (380 mg, 0.998 mmol) and LiBr (86.6 mg, 0.998 mmol) in DMF is heated at 150° C. for 10 min., cooled to room temperature, poured into 5 mL H2SO4, diluted with water and extracted with EtOAc. The extracts are combined, washed with water, dried over Na2SO4 and concentrated in vacuo. The resultant oil residue is passed through a silica gel pad, using a gradient elution of 100% EtOAc to 9:1 EtOAc:2.5% acetic acid in methanol, to afford the title product as a rust-yellow solid, 270 mg (78% yield), mp 220°-224° C., identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. washa gradient elution of 100% EtOAc to 9:1 EtOAc

Sources & evidence

ORD record
ord-690388e7a11144fc9e633f51bbb5d300
Source dataset
uspto-grants-2010_02
Patent number
US07666904B2

Reaction notes

Loading…