Dimethyl Sulfoxide → 4-n-butylidene-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene

HRID 2289429Notes

Reaction equation

HRID 2289429 reaction equation
[H-].[Na+].[CH3:3][S:4]([CH3:6])=O.O=[C:8]1[C:17]2[CH:16]=[CH:15]S[C:13]=2[CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl-].[NH4+].[CH3:20][CH2:21]OC(C)=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.C1COCC1>[CH:8](=[C:17]1[C:16]2[CH:15]=[CH:6][S:4][C:3]=2[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH2:9][CH2:20][CH3:21]

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 123415575,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one

Product 1

HCID 538249004-n-butylidene-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene

Reagents, catalysts & solvents 2

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of sodium hydride (NaH) (60% in Nujol, 0.69 g) and dimethyl sulfoxide (DMSO) (9 ml) was stirred at 70° C. for 2 hours. Abater cooling to r.t., THF (6 ml) and n-butyl-triphenylphosphonium bromide (7.26 g) were added thereto. The reaction mixture was stirred at r.t. for 1 hour, and then 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene (1.44 g) was added. The mixture was stirred at r.t. overnight and poured into a mixture of a saturated aqueous solution of ammonium chloride (NH4Cl) and AcOEt. The separated organic layer was washed with water and brine, and dried over MgSO4, and evaporated. The resulting oil was purified by chromatography on SiO2 (1% AcOEt in n-hexane as eluent). The fractions containing the object compound were combined and evaporated to give 4-n-butylidene-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene (1.15 g) as an oil.

Workup

  1. temperatureAbater cooling to r.t.
  2. stirringThe reaction mixture was stirred at r.t. for 1 hour
  3. stirringThe mixture was stirred at r.t. overnight
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe resulting oil was purified by chromatography on SiO2 (1% AcOEt in n-hexane as eluent)
  8. additionThe fractions containing the object compound
  9. customevaporated

Sources & evidence

ORD record
ord-1317df04eee948979b372f3834ede44b
Source dataset
uspto-grants-2000_07
Patent number
US06093710

Reaction notes

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