Potassium Iodide → HCID 69902352, compound

HRID 1008315Notes

Reaction equation

HRID 1008315 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:13][CH:12]=[C:11]([O:22]CCCCl)[CH:10]=1)[C:2]1[CH:7]=CC=CC=1.C([C:29]1[CH:45]=[CH:44][CH:43]=[CH:42][C:30]=1[O:31][C:32]1[C:33]([CH2:39][CH2:40][CH3:41])=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=1)#N.[I-].[K+].[C:48](=[O:51])([O-])[O-:49].[K+].[K+]>CC(=O)CC.CCOCC.CS(C)=O>[OH2:8].[CH2:13]([C:14]1[CH:15]=[C:16]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[C:11]([OH:22])=[CH:10][C:9]=1[O:8][CH2:1][CH2:2][CH2:7][O:38][C:34]1[C:33]([CH2:39][CH2:40][CH3:41])=[C:32]([CH:37]=[CH:36][CH:35]=1)[O:31][C:30]1[CH:42]=[CH:43][CH:44]=[CH:45][C:29]=1[C:48]([OH:49])=[O:51])[CH3:12]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 10610887HCID 10610887, compoundHCID 69903192HCID 69903192, compound

Product 1

HCID 69902352HCID 69902352, compoundYield 147.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-(benzyloxy)-2-(3-chloropropoxy)-5-(thiophen-3-yl)ethylbenzene (1.25 g, 3.23 mmol), 3-(2-cyanophenoxy)-2-propylphenol (0.82 g, 3.2 mmol), potassium iodide (0.21 g, 1.3 mmol), potassium carbonate (1.12 g, 8.08 mmol), and methyl sulfoxide (2 mL) in 2-butanone (10 mL) was refluxed for 60 h. The mixture was cooled to room temperature, diluted with ether, and washed with water. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 5% ethyl acetate/95% hexane) of the residue provided 1.31 g (67%) of the title product as a colorless oil. 1H NMR (CDCl3) δ 7.66 (d, J=7.8. Hz, 1H), 7.57 (d, J=2.9 Hz, 1H), 7.48 (d, J=5.2 Hz, 1H), 7.45-7.25 (m, 8H), 7.20 (t, J=8.2 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.77 (d, J=8.6 Hz, 1H), 6.64 (s, 1H), 6.63 (d, J=6.4 Hz, 1H), 5.11 (s, 2H), 4.26 (t, J=6.0 Hz, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.65 (m, 4H), 2.36 (quintet, J=5.9 Hz, 2H), 1.58 (hextet, J=7.5 Hz, 2H), 1.24 (t, J=7.5 Hz, 3H), 0.95 (t, J=7.3 Hz, 3H); MS FD m/e 603 (p); IR (CHCl3, cm−1) 2967, 2250, 1613, 1501. Anal. Calcd for C38H37NO4S: C, 75.59; H, 6.18; N, 2.32. Found: C, 74.65; H, 6.21; N, 2.57.

Workup

  1. temperaturewas refluxed for 60 h
  2. washwashed with water
  3. dry with materialThe organic layer was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b612bf4919a840aa8fb7d1e5e868c220
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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