1,2-Dimethoxyethane → 3-(7-Chloro-benzofuran-4-yl)-acrylic acid methyl ester

HRID 1602385Notes

Reaction equation

HRID 1602385 reaction equation
C[C:2](P(OC)(O)=O)([C:4]([O-:6])=[O:5])[CH3:3].[H-].[Na+].[Cl:14][C:15]1[CH:16]=[CH:17][C:18](C=O)=[C:19]2[C:23]=1[O:22][CH:21]=[CH:20]2.[CH3:26]OCCOC>>[CH3:26][O:6][C:4](=[O:5])[CH:2]=[CH:3][C:18]1[C:19]2[CH:20]=[CH:21][O:22][C:23]=2[C:15]([Cl:14])=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 80711,2-Dimethoxyethane3×HCID 24758Sodium hydrideHCID 19611677HCID 19611677, compound2×HCID 53413272Trimethylphosphonoacetate

Product 1

HCID 537840183-(7-Chloro-benzofuran-4-yl)-acrylic acid methyl ester

Procedure

Trimethylphosphonoacetate (363 mg) in dry DME (1 ml) was added dropwise to a suspension of sodium hydride (60%; 329 mg) in dry DME (20 ml) at 0° under nitrogen. The resulting white precipitate was stirred for 40 mins at room temperature, then a solution of 7-chloro-benzofuran-4-carbaldehyde (intermediate 2) (1.238 g) in dry DME (15 ml) was added at room temperature over 1 min. The mixture was heated under reflux for 2 h, cooled to room temperature, then partitioned between water (150 ml) and ether (100 ml). The. combined organic extracts were washed with brine (100 ml) and dried (MgSO4). The solvent was evaporated to give the title compound as a colourless solid (1.59 g)

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled to room temperature
  4. custompartitioned between water (150 ml) and ether (100 ml)
  5. washcombined organic extracts were washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ded68973f0654c0cb1944dcf57465515
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

Loading…