N-Iodosuccinimide → HCID 19389258, compound

HRID 1757688Notes

Reaction equation

HRID 1757688 reaction equation
[C:1]1(C#CC2(O)CCCC2)[CH:6]=CC=C[CH:2]=1.[CH2:15]1[C:20](=[O:21])N(I)[C:17](=O)[CH2:16]1.CC1C=CC(S(O[I:34](O)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=O)=O)=CC=1>CO.C(OCC)C>[C:40]1(=[C:35]([I:34])[C:20]([C:15]2[CH:6]=[CH:1][CH:2]=[CH:17][CH:16]=2)=[O:21])[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 1411771-(Phenylethynyl)-1-cyclopentanolHCID 325434[Hydroxy(tosyloxy)iodo]benzene

Product 1

HCID 19389258HCID 19389258, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1-Phenylethynyl-l-cyclopentanol (352 mg, 1.89 mmol) was dissolved in 20 mL of methanol. NIS (514 mg, 2.29 mmol) and HTIB (96 mg, 0.24 mmol) were added in one portion to the stirring solution. The reaction was protected from light and stirred at room temperature for 18 hours. The reaction mixture was diluted with 75 mL of diethyl ether and washed with 25 mL of 5% Na2S2O3 solution and followed by 3×25 mL of water. The organic solution was dried with MgSO4 and following filtration it was evaporated under vacuum to give a light green oil. The residue was subjected to a silica gel (40-40 mesh) column chromatography. Iodobenzene was eluted first with hexanes. The product was eluted next with 1:1 mixture Et2O/ hexanes to yield a light green oil after solvent evaporation (329 mg, 56%). The product was characterized by spectroscopy: 1H-NMR (CDCl3) δ1.75-1.84 (m, 4H), 2126 (t,7 Hz, 2H), 2154 (t, 7 Hz, 2H), 7.47 (t, 6 Hz, 2H), 7.67 (d, 6 Hz, 1H), 7.91(d, 6 Hz, 2H); 13C-NMR (CDCl3) δ25.22, 28.53, 34.02, 40.85, 85.60, 128.57, 128.61, 129.70, 133.23, 133.30, 134.50, 158.84, 1.92.83; IR (CHCl3) 1655 (s), 1590 (w), 1400 (w), 1300 (m), 1250 (s),1220 (m), 1170 (m), 1050 (w), 1025 (w), 820 (w), 750 (s) cm-1 ; MS m/z(rel. int.) 312 (M+, 2), 185 (M-I, 20), 184 (M-I-H, 11), 157 (13), 129 (11), 127 (I, 18), 115 (18), 105 (C6H5CO, 35), 80 (16), 77 (C6H5, 100); Anal. calcd for C13 H13IO: C, 49.98; H, 4.21. Found: C, 50.54: H, 4.21.

Workup

  1. washwashed with 25 mL of 5% Na2S2O3 solution
  2. dry with materialThe organic solution was dried with MgSO4
  3. filtrationfiltration it
  4. customwas evaporated under vacuum
  5. customto give a light green oil
  6. washIodobenzene was eluted first with hexanes
  7. washThe product was eluted next with 1:1 mixture Et2O/ hexanes
  8. customto yield a light green oil
  9. customafter solvent evaporation (329 mg, 56%)

Sources & evidence

ORD record
ord-c2646ce3d8b04f308815ea8514e659ca
Source dataset
uspto-grants-1995_08
Patent number
US05446203

Reaction notes

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