Iodoethane → HCID 21877322, compound

HRID 2181540Notes

Reaction equation

HRID 2181540 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][C:3]=1[CH2:19][OH:20].[OH-].[K+].I[CH2:24][CH3:25]>CS(C)=O.O>[Br:1][C:2]1[C:3]([CH2:19][O:20][CH2:24][CH3:25])=[CH:4][C:5]([O:10][CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:18])[CH3:17])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 22486246HCID 22486246, compound

Product 1

HCID 21877322HCID 21877322, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The crude benzyl alcohol was stirred with a solution of potassium hydroxide (800 mg, 14.4 mmol) in DMSO (8 mL). Iodoethane (580 mL, 7.2 mmol) was added, and the reaction stirred for 16 h before it was diluted with H2O (30 mL) and extracted with ether (2×30 mL). Organics were washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (15% EtOAc/hexanes) gave 1.30 g (92%) of the title compound as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H), 7.03 (s, 1H), 5.26 (s, 2H), 4.48 (s, 2H), 3.85 (s, 3H), 3.79 (t, 2H, J=8.4 Hz), 3.58 (q, 2H, J=6.9 Hz), 1.26 (t, 3H, J=6.9 Hz), 0.95 (t, 2H, J=8.4 Hz), −0.01 (s, 9H).

Workup

  1. extractionextracted with ether (2×30 mL)
  2. washOrganics were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f11cfa1df931488e9a2da7225345dcd7
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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