Sodium hydride → HCID 70238623, compound

HRID 322023Notes

Reaction equation

HRID 322023 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].BrC[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][O:12][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 262953-Phenoxybenzyl alcoholHCID 11043787HCID 11043787, compound

Product 1

HCID 70238623HCID 70238623, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-phenoxybenzylalcohol (545 mg; 2.72 mmol) in DMF (5 ml) was added NaH (92 mg; 3.1 mmol; 80% dispersion in oil) and ethyl(E)-3-(2-(bromomethyl)phenyl)-2-propenoate (810 mg; 3.0 mmol). After 6 h at r.t., 20 mg extra NaH was added. The final mixture was stirred at r.t. for 10 h then quenched using 0.3 ml of AcOH. The mixture was diluted with Et2O (25 ml), washed with water (3×20 ml) and brine, dried over MgSO4 and concentrated. Flash chromatography with EtOAc:toluene 5:95 afforded the desired material.

Workup

  1. customthen quenched
  2. additionThe mixture was diluted with Et2O (25 ml)
  3. washwashed with water (3×20 ml) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5b5a0eea4c24ee785ab9c1680322a32
Source dataset
uspto-grants-2001_04
Patent number
US06211197B1

Reaction notes

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