Tetrahydrofuran → HCID 20329658, compound

HRID 2057961Notes

Reaction equation

HRID 2057961 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][C:14]([C:16]([O:18]CC)=[O:17])=[CH:13][C:12]=3[CH:21]=2)=[CH:4][CH:3]=1.O1CCCC1>[Na].[Hg].C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH:14]([C:16]([OH:18])=[O:17])[CH2:13][C:12]=3[CH:21]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 20329637HCID 20329637, compound

Product 1

HCID 20329658HCID 20329658, compound

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 702EthanolSolvent

Procedure

61.5 g of 2.5% sodium amalgam was added in portions to a mixture of 6.7 g of 18A, 270 ml of tetrahydrofuran and 90 ml of ethanol. The mixture was stirred for 20 hours at room temperature. The solvent was evaporated under reduced pressure. The residue was dissolved in 1 liter of hot water containing 4 ml of saturated sodium hydroxide solution. The mixture was filtered, the filtrate was cooled with an ice bath, and acidified to pH=2. The mixture was stirred for 30 minutes, the resulting solid was collected, washed with water and dried (reduced pressure, P2O5, refluxing acetone) to give 2,3-dihydro-5-(4-chlorophenyl)-2-benzofurancarboxylic acid (18B), mp: 147°-149° C.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 1 liter of hot water containing 4 ml of saturated sodium hydroxide solution
  3. filtrationThe mixture was filtered
  4. temperaturethe filtrate was cooled with an ice bath
  5. stirringThe mixture was stirred for 30 minutes
  6. customthe resulting solid was collected
  7. washwashed with water
  8. customdried
  9. temperature(reduced pressure, P2O5, refluxing acetone)

Sources & evidence

ORD record
ord-d198fe109d7946cda9d7c61ff7a65942
Source dataset
uspto-grants-1980_07
Patent number
US04213999

Reaction notes

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