Benzaldehyde, 4-(phenylmethoxy)- → HCID 67204211, compound

HRID 545453Notes

Reaction equation

HRID 545453 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13](Br)[CH:12]=[CH:11]2.[CH2:19]([O:26]C1C=CC(C=O)=CC=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:35](=[O:37])=[O:36].[CH3:38][C:39]([CH3:41])=O>C1CCCCC1.C1COCC1>[OH:26][CH:19]([C:13]1[CH:12]=[CH:11][C:10]2[C:15](=[CH:16][CH:17]=[C:8]([O:7][CH3:6])[CH:9]=2)[CH:14]=1)[C:20]1[CH:25]=[CH:24][C:23]([C:35]([O:37][CH2:5][C:4]2[CH:41]=[CH:39][CH:38]=[CH:2][CH:3]=2)=[O:36])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 787862-Bromo-6-methoxynaphthaleneHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 67204211HCID 67204211, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-60 °C

Procedure

n-BuLi (15 mL of a 2.0 M solution in cyclohexane, 30 mmol) was added dropwise to a solution of 6-methoxy-2-bromonaphthalene (5.9 g, 25 mmol) in 200 mL of dry THF cooled in dry ice-acetone bath. After 15 min, 4-benzyloxybenzaldehyde (5.3 g, 25 mmol) was added. After stirring for an additional 30 min, the cold bath was allowed to slowly warm to −60° C. over 30 min. The reaction vessel was removed from the cold bath for 10 min, then cooled to −78° C. The reaction mixture was quenched with aq ammonium chloride, diluted with hexanes and allowed to stand at 4° C. for 48 h. Chloroform was added to dissolve the precipitate. The mixture was dried with sodium sulfate and concentrated to about 100 mL, upon which a precipitate formed. Hexanes (100 mL) was added and the solid was filtered and washed with a mixture of 100 mL of hexanes and 50 mL of EtOAc to provide the title compound as a racemic mixture. LCMS (ESI): m/z 353.1 [M−OH]+. 1H NMR (500 MHz, CD2Cl2): δ (ppm) 7.82 (s, 1H), 7.74 (m, 2H), 7.46-7.32 (m, 8H), 7.16 (m, 2H), 6.96 (d, J=8.7 Hz, 2H), 5.94 (d, J=2.3 Hz, 1H), 5.07 (s, 2H), 3.92 (s, 3H).

Workup

  1. customThe reaction vessel was removed from the cold bath for 10 min
  2. temperaturecooled to −78° C
  3. customThe reaction mixture was quenched with aq ammonium chloride
  4. additiondiluted with hexanes
  5. waitto stand at 4° C. for 48 h
  6. additionChloroform was added
  7. dissolutionto dissolve the precipitate
  8. dry with materialThe mixture was dried with sodium sulfate
  9. concentrationconcentrated to about 100 mL, upon which a precipitate
  10. customformed
  11. filtrationthe solid was filtered
  12. washwashed with a mixture of 100 mL of hexanes and 50 mL of EtOAc

Sources & evidence

ORD record
ord-2ef659099ed8499cbc4a2e4d0eec5547
Source dataset
uspto-grants-2011_05
Patent number
US07935713B2

Reaction notes

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