2,3-Dihydro-1lambda6-benzothiophene-1,1-dione → 2,3-Dihydrobenzo(b)thiophene

HRID 256417

Reaction equation

HRID 256417 reaction equation
O=[S:2]1(=O)[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)C>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 2844232,3-Dihydro-1lambda6-benzothiophene-1,1-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 783192,3-Dihydrobenzo(b)thiopheneYield 58%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 22.3 g (132 mmole) of the product of Part (ii) in 200 ml tetrahydrofuran was added dropwise with stirring to a mixture of 5.81 g (145 mmole) lithium aluminum hydride (95%) in 400 ml dry ethyl ether, at a rate sufficient to maintain gentle reflux. Refluxing was continued for 30 minutes. The mixture was cooled in ice and quenched by cautious addition of 6 ml water followed by 6 ml 15% (w/v) sodium hydroxide and 18 ml water. The resulting mixture was filtered, the organic phase washed with brine, dried (Na2SO4) and evaporated to provide a yellow oil which was distilled to yield 10.4 g (58%) product, b.p. 129°-131° C. The structure was verified by 1H-NMR spectroscopy.

Workup

  1. temperatureto maintain gentle reflux
  2. temperatureRefluxing
  3. temperatureThe mixture was cooled in ice
  4. customquenched by cautious addition of 6 ml water
  5. filtrationThe resulting mixture was filtered
  6. washthe organic phase washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto provide a yellow oil which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-1e959b03d50340799e0ebf38d41b8c4b
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Linked notes

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