Trimethyl orthoformate → HCID 20306074, compound

HRID 1732325Notes

Reaction equation

HRID 1732325 reaction equation
[Cl:1][C:2]1[C:12]([C:13](=[O:19])[C:14]2[S:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:5]2[CH2:6][CH:7](C=O)[O:8][C:4]=2[C:3]=1[Cl:20].CO[CH:23]([O:26][CH3:27])[O:24][CH3:25].C(=O)([O-])O.[Na+]>[Cl-].[Cs+]>[CH3:27][O:26][CH:23]([O:24][CH3:25])[CH:7]1[CH2:6][C:5]2[CH:11]=[C:12]([C:13](=[O:19])[C:14]3[S:18][CH:17]=[CH:16][CH:15]=3)[C:2]([Cl:1])=[C:3]([Cl:20])[C:4]=2[O:8]1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 12747909HCID 12747909, compound

Product 1

HCID 20306074HCID 20306074, compound

Reagents, catalysts & solvents 1

HCID 24293Cesium ChlorideSolvent

Procedure

6,7-Dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxaldehyde (3.2 g., 0.01 mole) is dissolved in methanolic cesium chloride (25 ml., 0.4 M). Trimethylorthoformate (2.12 g., 0.02 mole) is added and the solution is stirred (magnetically) at room temperature for 30 minutes and then poured into aqueous sodium hydrogen carbonate (50 ml.). The mixture is extracted with ether (2×50 ml.). The ether extracts are combined, washed with brine (2×15 ml.), dried over MgSO4 and distilled at reduced pressure to give the 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)benzofuran-2-carboxaldehyde dimethylacetal.

Workup

  1. extractionThe mixture is extracted with ether (2×50 ml.)
  2. washwashed with brine (2×15 ml.)
  3. dry with materialdried over MgSO4
  4. distillationdistilled at reduced pressure

Sources & evidence

ORD record
ord-50da7001e3a94aec8bc5d5984168c595
Source dataset
uspto-grants-1980_12
Patent number
US04237144

Reaction notes

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