Sodium Hydroxide → HCID 86762126, compound

HRID 2041853Notes

Reaction equation

HRID 2041853 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].[F:16][C:17]([F:44])([F:43])[C:18]([F:42])([F:41])[C:19]([F:40])([F:39])[C:20]([F:38])([F:37])[C:21]([F:36])([F:35])[C:22]([F:34])([F:33])[C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[CH2:25][CH2:26][CH2:27]I>CS(C)=O>[F:29][C:24]([F:30])([C:23]([F:31])([F:32])[C:22]([F:33])([F:34])[C:21]([F:35])([F:36])[C:20]([F:37])([F:38])[C:19]([F:39])([F:40])[C:18]([F:42])([F:41])[C:17]([F:44])([F:43])[F:16])[CH2:25][CH2:26][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5319562Methyl-P-CoumarateHCID 111575823-(Perfluorooctyl)propyl iodide

Product 1

HCID 86762126HCID 86762126, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(E)-Methyl 3-(4-hydroxyphenyl)acrylate (166 mg, 0.93 mmol) was added to dry DMSO (10 mL) and stirred under nitrogen in a round bottom flask. Crushed sodium hydroxide (44 mg, 1.1 mmol) was added. After 30 minutes, 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-11-iodoundecane (500 mg, 0.85 mmol) was added. The reaction was allowed to stir overnight. Washed with water and extracted with dichloromethane to yield an oil. This crude product was purified on a silica column using hexanes with increasing amounts of ethyl acetate as the eluent. A white solid was isolated (418 mg, 77% yield). 1H NMR (400.14 MHz, CDCl3) δ 7.65 (d, J=16.0 Hz), 7.48 (d, J=8.75 Hz, 2H), 6.90 (d, J=8.75 Hz, 2H), 6.32 (d, J=16.0 Hz), 4.07 (t, J=5.90 Hz, 2H), 3.80 (3H), 2.40-2.20 (m, 2H), 2.18-2.05 (m, 2H).

Workup

  1. stirringto stir overnight
  2. washWashed with water
  3. extractionextracted with dichloromethane
  4. customto yield an oil
  5. customThis crude product was purified on a silica column
  6. customA white solid was isolated (418 mg, 77% yield)

Sources & evidence

ORD record
ord-f832f5c98e154e4391f0a3536056e17a
Source dataset
uspto-grants-2013_11
Patent number
US08586208B2

Reaction notes

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