Tetrahydrofuran → HCID 20144491, compound

HRID 649017Notes

Reaction equation

HRID 649017 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[C:5]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:6]=2[S:7][CH:8]=1.O1CCCC1.C([Li])CCC.C([O-])(O)=O.[Na+]>CCCCCC>[C:3]([C:4]1[C:5]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:6]=2[S:7][CH:8]=1)#[CH:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 20144461HCID 20144461, compoundHCID 178418339Butyllithium

Product 1

HCID 20144491HCID 20144491, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

0.6 g of 3-(dibromovinyl)-7-methylbenzo[b]thiophene are dissolved in abs. tetrahydrofuran and 3.38 ml of a 15% solution of n-butyllithium in n-hexane are added dropwise under inert gas and at -78°. Stirring is continued for one hour at -78° and the mixture subsequently warmed to room temperature, poured into saturated aq. NaHCO3 and extracted with ether. The organic phase is washed, dried, concentrated and directly further reacted.

Workup

  1. extractionextracted with ether
  2. washThe organic phase is washed
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb66eba03164279873631165f2d56a4
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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