7-Methoxybenzo[b]thiophene → HCID 22171216, compound

HRID 1822965Notes

Reaction equation

HRID 1822965 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[S:10][CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.CC1(C)CCCC(C)(C)N1[Li].Cl([F:27])(=O)(=O)=O>C1COCC1>[F:27][C:9]1[S:10][C:11]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 110842177-Methoxybenzo[b]thiopheneHCID 178418821HCID 178418821, compound

Product 1

HCID 22171216HCID 22171216, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1-benzothien-7-yl methyl ether (230 mg, 1.40 mmol) in dry THF (5 mL) was added dropwise to a freshly prepared solution of 2,2,6,6 tetramethyl-lithio-piperidine (1.68 mmol) in THF (10 mL) at −78° C. The resulting solution was stirred at this temperature for 30 mins before perchloryl fluoride gas was condensed into the reaction. After the strong exotherm had stopped the mixture was allowed to stir at −78° C. for a further 30 mins. After this time the reaction was quenched with NH4Cl (sat, 20 mL) and diluted with diethyl ether. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane to yield a colourless oil (128 mg, 50%); δH (300 MHz, CDCl3) 7.32–7.20 (2H, m, Ar), 6.80–6.62 (2H, m, Ar), 3.95 (3H, s, OCH3).

Workup

  1. customcondensed
  2. custominto the reaction
  3. customAfter this time the reaction was quenched with NH4Cl (sat, 20 mL)
  4. additiondiluted with diethyl ether
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-5a04101ae2894cfa96058068caaba782
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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