Carbon Tetrachloride → HCID 14685359, compound

HRID 893801Notes

Reaction equation

HRID 893801 reaction equation
C1CC1.Cl[CH2:5][C:6]([C:10]1[S:11][CH:12]=[CH:13][C:14]=1[CH3:15])=[C:7]([CH3:9])[CH3:8].C(Cl)(Cl)(Cl)[Cl:17]>>[Cl:17][C:6]1([C:10]2[S:11][CH:12]=[CH:13][C:14]=2[CH3:15])[CH2:5][C:7]1([CH3:9])[CH3:8]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 6351CyclopropaneHCID 14685374HCID 14685374, compound

Product 1

HCID 14685359HCID 14685359, compound

Procedure

The cyclopropane produced in b) (0.40 g, 2.0 mmol) was stirred with gravity silica (0.15 g) in carbon tetrachloride (10 cm3) at 20° C. The silica developed a purple/black coloration within 30 min while the solution remained colourless. After 18 h at 20° C. no starting material remained. The silica was removed by filtration and the carbon tetrachloride evaporated to give a product characterised as 1-chloro-2-(3-methylthien-2-yl)-3-methylbut-2-ene (0.33 g, 82%) as the only product, which was pure by n.m.r. (Found: M+ +200.0417. C10H13SCl requires M, 200.0426) which showed νmax (film) 708 s, 1256 m, 1444 m, 1700 m and 29922 m cm-1 ; δH (CCl4) 1.65 (3H, s), 1.98 (3H, s), 2.06 (3H, s), 4.20 (2H, s), 6.72 (1H, d, J 5 Hz), 7.03 (1H, d, J 5 Hz); m/z 200 (M+), 165 (M+ -Cl).

Workup

  1. customwithin 30 min
  2. customThe silica was removed by filtration
  3. customthe carbon tetrachloride evaporated
  4. customto give a product
  5. customνmax (film) 708 s, 1256 m, 1444 m, 1700 m and 29922 m cm-1

Sources & evidence

ORD record
ord-5b52c0ae37f74cefb801fa5d276e1866
Source dataset
uspto-grants-1992_06
Patent number
US05126461

Reaction notes

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