Sodium Iodide → HCID 23111765, compound

HRID 1163278Notes

Reaction equation

HRID 1163278 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>O.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([CH:10]=1)[O:17][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 23111765HCID 23111765, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(Benzyloxy)-2-hydroxybenzaldehyde (5.8 g), ethyl 4-bromobutyrate (7.1 mL), potassium carbonate (10.5 g) and sodium iodide (3.8 g) were added to N,N-dimethylformamide (50 mL), and the mixture was stirred overnight at room temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane) to give the title compound (8.2 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-ae73c2371dfb479e94f06ef8db31141d
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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