4,5,6,7-Tetrahydro-4-oxothionaphthene → HCID 22474025, compound

HRID 2183627Notes

Reaction equation

HRID 2183627 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[S:6]1[CH:10]=[CH:9][C:8]2C(=O)CC[CH2:14][C:7]1=2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:4]=[C:3]1[C:8]2[CH:9]=[CH:10][S:6][C:7]=2[CH2:14][CH2:1][CH2:2]1

Participants

5

Reactant 2

HCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 178418339Butyllithium

Product 1

HCID 22474025HCID 22474025, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5M solution in hexanes; 105.3 ml) was added dropwise under nitrogen at 0° C. over 30 minutes to a stirred solution of methyltriphenyl-phosphonium bromide (75.16 g) in tetrahydrofuran (250 ml), then the mixture was stirred at ambient temperature for 90 minutes. A solution of 6,7-dihydrobenzo[b]thiophen-4(5H)-one (20 g) in tetrahydrofuran (200 ml) was added, the mixture was stirred at ambient temperature for 1 hour, then it was heated under reflux for 24 hours and cooled to ambient temperature. The solvents were removed in vacuo and the residue was purified by flash chromatography over silica using a 98:2 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to give 4-methylene-4,5,6,7-tetrahydrobenzo[b]thiophene (8.8 g) as a yellow oil which was used without further purification.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. temperatureit was heated
  3. temperatureunder reflux for 24 hours
  4. temperaturecooled to ambient temperature
  5. customThe solvents were removed in vacuo
  6. customthe residue was purified by flash chromatography over silica using
  7. additiona 98:2 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane as eluant
  8. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-ba18b06bcdf643e6814ad7bd44229ccc
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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