Tetrahydrofuran → HCID 53656486, compound

HRID 650585Notes

Reaction equation

HRID 650585 reaction equation
[CH2:1]([O:3][C:4]([CH2:6]P(=O)(OCC)OCC)=[O:5])[CH3:2].[H-].[Na+].O1CCCC1.O=[C:23]1[C:31]2[CH:30]=[CH:29][S:28][C:27]=2[CH2:26][CH2:25][CH2:24]1>C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([CH:6]=[C:23]1[C:31]2[CH:30]=[CH:29][S:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 834184,5,6,7-Tetrahydro-4-oxothionaphthene

Product 1

HCID 53656486HCID 53656486, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl ethoxycarbonylmethylphosphonate (8.47 ml) was dropwise added to a mixture of sodium hydride (60%, 1.71 g) and tetrahydrofuran (THF) (50 ml) at room temperature (r.t.) under nitrogen atmosphere, and the mixture was stirred under the same condition for 30 minutes. To the reaction mixture was added 4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene (5.00 g) in a portion, and the whole mixture was stirred at r.t. for 3 hours. The reaction mixture was poured into a mixture of water and ethyl acetate (AcOEt). The separated organic layer was washed with water and brine, and dried over magnesium sulfate (MgSO4), and dried in vacuo to precipitate. The resulting precipitate was washed with isopropyl ether (iPE) to give 4-ethoxycarbonylmethylidene-4,5,6,7-tetrahydrobenzo[b]thiophene (5.91 g).

Workup

  1. stirringthe whole mixture was stirred at r.t. for 3 hours
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate (MgSO4)
  4. customdried in vacuo
  5. customto precipitate
  6. washThe resulting precipitate was washed with isopropyl ether (iPE)

Sources & evidence

ORD record
ord-399c056456474408a3a759311ad7c329
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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