Water → HCID 178506641, compound

HRID 610397Notes

Reaction equation

HRID 610397 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[Li:10]CCCC.ClB(Cl)C1CCCC1.O>CCOCC>[S:1]1[C:5]([Li:10])=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 7221Benzo(B)ThiopheneHCID 5326172Borane, dichlorocyclopentyl-HCID 178418339Butyllithium

Product 1

HCID 178506641HCID 178506641, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-90 °C

Procedure

A dry 100 mL round-bottomed flask equipped with a mechanical stirrer, a reflux condenser, a low temperature thermometer and a silicone rubber septum was flushed with argon. 2-benzo[B]thienyllithium was prepared in situ from 1.1 g of benzo[B]thiophene (8.21 mmol) and 3.3 mL of 2.5 m solution of n-BuLi (in hexanes) in 20 mL of ether. The mixture was cooled to -90° C. and the solution of dichlorocyclopentylborane obtained in step 1 was added over 10 min while stirring was maintained. The mixture was brought to 20° C. and stirred for 2 h at this temperature. Distilled water (20 mL) was added with vigorous stirring. The top layer formed was separated and discarded. The aqueous layer was poured into 30 mL of saturated solution of NME4CL and shaken. The precipitate formed was filtered, washed with 60 ml of distilled water, and recrystallized from acetone/methanol=3/2 yielding 1.2 g (79%) of white crystalline solid. m.p. 234-236° C. 1H NMR (D6 -DMSO, 200 MHz) δ 7.69 (d, J=7.6 Hz, 3H), 7.57 (d, J=7.6 Hz, 3H), 7.14 (t, J=7.4 Hz, 3H), 7.07 (s, 3H), 7.04 (t, J=7.4 Hz, 3H), 3.04 (s, 12H), 1.85 (m, 2H), 1.65 (m, 1H), 1.37 (br s, 6H). 13C NMR (D6 -DMSO, 50 MHz) δ 141.9, 124.1, 122.5, 121.4, 120.9, 54.51 (t, J=4 HZ), 31.38, 27.34. 11B NMR (DMSO, 128 MHz) δ -30.36. Anal. Calcd. for C33H36BNS3 : C, 71.59; H, 6.55; N, 2.53; S, 17.37. Found: C, 71.50; H, 6.63; N, 2.53; S, 17.30.

Workup

  1. customA dry 100 mL round-bottomed flask equipped with a mechanical stirrer, a reflux condenser
  2. customa low temperature thermometer and a silicone rubber septum was flushed with argon
  3. temperaturewas maintained
  4. customwas brought to 20° C.
  5. stirringstirred for 2 h at this temperature
  6. customThe top layer formed
  7. customwas separated
  8. additionThe aqueous layer was poured into 30 mL of saturated solution of NME4CL
  9. stirringshaken
  10. customThe precipitate formed
  11. filtrationwas filtered
  12. washwashed with 60 ml of distilled water
  13. customrecrystallized from acetone/methanol=3/2 yielding 1.2 g (79%) of white crystalline solid

Sources & evidence

ORD record
ord-edbe34f5131a4ce991a565184b2bbd84
Source dataset
uspto-grants-1999_12
Patent number
US05998496

Reaction notes

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