Butyl Chloride → HCID 19759867, compound

HRID 1586857Notes

Reaction equation

HRID 1586857 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[S:7]1[C:11]2S[CH:13]=[CH:14][C:10]=2[CH2:9][CH2:8]1.C(Cl)CCC>O.CO>[S:3]1(=[O:5])(=[O:2])[C:11]2[S:7][CH:8]=[CH:9][C:10]=2[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 8005Butyl ChlorideHCID 10219490HCID 10219490, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 19759867HCID 19759867, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Oxone® (570 g, 0.92 mol) in H2O (2 L) was added to a stirred solution of 2,3-dihydrothieno[2,3-b]thiophene (44 g, 0.31 mol) in methanol (1 L). The reaction was stirred for 1.5 h at room temperature, and then extracted with ethyl acetate (5×1 L). The combined extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give a soft solid. This was treated with n-butyl chloride and filtered to give the title compound as a light tan solid (35 g, 65%). 1H NMR (300 MHz,DMSO-d6) 3.30(2H,t), 3.95(2H,t), 7.10(1H,d), 8.05(1H,d).

Workup

  1. extractionextracted with ethyl acetate (5×1 L)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a soft solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-286a7d2b3f0045ca9c71599db7d2878a
Source dataset
uspto-grants-1993_06
Patent number
US05216020

Reaction notes

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