Iodoethane → HCID 69633354, compound

HRID 1373761Notes

Reaction equation

HRID 1373761 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22])[CH:2]=[CH2:3].I[CH2:24][CH3:25].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:24][CH3:25])=[CH:7][C:6]=1[N:12]1[C:13](=[O:22])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]1=[O:21])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69633424HCID 69633424, compound

Product 1

HCID 69633354HCID 69633354, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of Example 84A (0.63 g, 2.13 mmol), iodoethane (0.68 mL, 8.52 mmol) and K2CO3 (1.47 g, 10.65 mmol) in acetone (50 mL) were stirred, and refluxed for 3 hours, and cooled. The solution was filtered, and dried with silica gel powder (10 g). 15% Ethyl acetate in hexanes (1 L) and 20% ethyl acetate in hexanes (1 L) were used to run flash chromatography. The title compound was obtained (320 mg, 46%). MS (DCI) m/z 324.07 (M+H)+; 1H NMR (300 MHz, CDCl3) δ ppm 1.39 (t, J=7.12 Hz, 3 H) 4.00 (q, J=7.12 Hz, 2 H) 4.46–4.55 (m, 2 H) 5.07–5.30 (m, 2 H) 5.88 (m, 1 H) 6.82 (dd, J=2.54, 0.85 Hz, 1 H) 6.93–6.96 (m, 2 H) 7.75–7.80 (m, 2 H) 7.94 (dd, J=5.42, 3.05 Hz, 2 H).

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturecooled
  3. filtrationThe solution was filtered
  4. customdried with silica gel powder (10 g)

Sources & evidence

ORD record
ord-c6286d273c724179b7958a10e90b58d3
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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