2-Naphthalenecarboxaldehyde → HCID 69426752, compound

HRID 1592292Notes

Reaction equation

HRID 1592292 reaction equation
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])C=CC=CC=1.[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[CH:38]=O>C1(C)C=CC=CC=1>[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[CH:38]=[CH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 62012-NaphthalenecarboxaldehydeHCID 256127tert-Butyl (triphenylphosphoranylidene) acetate

Product 1

HCID 69426752HCID 69426752, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of tert-butyl triphenylphosphoranediylacetate (8.82 g, 23.4 mmol) in toluene (15 mL) was added a solution of 2-naphthaldehyde (2.82 g, 18.0 mmol) in toluene (15 mL). The mixture was stirred at room temperature for 18 hr and filtered. The filtrate was concentrated, subjected to silica gel column chromatography (ethyl acetate/hexane=1/30) and recrystallized (acetonitrile/water=1/2) to give the title compound as a colorless paste (4.1 g, yield 91%), melting point: 74-75° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customrecrystallized (acetonitrile/water=1/2)

Sources & evidence

ORD record
ord-f5180a4c36ce488fbafeb192f6f1ae93
Source dataset
uspto-grants-2007_11
Patent number
US07291752B2

Reaction notes

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