2-Naphthalenecarboxaldehyde → HCID 67393249, compound

HRID 907383Notes

Reaction equation

HRID 907383 reaction equation
C(OP([CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1)(OCC)=O)C.[H-].[Na+].[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[CH:32]=O>C1COCC1>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1/[CH:32]=[CH:9]/[C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 24758Sodium hydrideHCID 10946061Methyl 4-(diethoxyphosphorylmethyl)benzoate

Product 1

HCID 67393249HCID 67393249, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[(diethoxyphosphoryl)methyl]benzoate (916 mg, 3.20 mmol; see Preparation 4(i) above) in THF (20 mL, dry) under nitrogen atmosphere was added a sodium hydride (520 mg, 60% dispersion in oil, 13.00 mmol) at 0° C. 2-Naphthaldehyde (500 mg, 3.20 mmol) was dissolved in THF (10 mL, dry) then added dropwise to the reaction mixture at 0° C. under N2 and the reaction mixture stirred at room temperature for 1 h followed by quenching with water. The pH level of the mixture was adjusted to pH 4 by the dropwise addition of HCl(conc.) with stirring at 0° C. TLC analysis showed that it was the required product (282 mg). Extraction of the water layer with ethyl acetate followed by drying (MgSO4) gave the sub-title compound (total amount 846 mg, 92%), m.p.=195-198° C.

Workup

  1. additionthen added dropwise to the reaction mixture at 0° C. under N2
  2. customby quenching with water
  3. additionThe pH level of the mixture was adjusted to pH 4 by the dropwise addition of HCl(conc.)
  4. stirringwith stirring at 0° C
  5. extractionExtraction of the water layer with ethyl acetate
  6. dry with materialby drying (MgSO4)

Sources & evidence

ORD record
ord-2eb6ee0b93524d22a893e92200bd5899
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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