Tetrahydrofuran → 2-Vinyl-6-methoxynaphthalene

HRID 400339

Reaction equation

HRID 400339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](C=O)=[CH:8][CH:7]=[CH:6]2.[CH2:15]1COC[CH2:16]1>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:15]=[CH2:16])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 128430406-Methoxynaphthalene-1-carbaldehyde

Product 1

HCID 6035352-Vinyl-6-methoxynaphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Methoxy-naphthaldehyde (432 mg, 2.35 mmol) is added to a solution of instantaneous ylide (Ph3P+Br−+NaNH2, 1.48 g, 2.4 mmol) in anhydrous THF (5 ml). After one hour of stirring at ambient temperature, it is diluted with ether, it is filtered on Celite, and it is chromatographed (hexane/AcOEt 5:1) to obtain 6-methoxy-2-vinyl-naphthalene (390 mg, 90%).

Workup

  1. filtrationis filtered on Celite, and it
  2. customis chromatographed (hexane/AcOEt 5:1)

Sources & evidence

ORD record
ord-26a379baa01243c797c0116c08dda5b4
Source dataset
uspto-grants-2014_06
Patent number
US08741593B2

Linked notes

Loading…