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Chemical Structure| 3453-33-6 Chemical Structure| 3453-33-6

Structure of 6-Methoxy-2-Naphthaldehyde
CAS No.: 3453-33-6

Chemical Structure| 3453-33-6

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Product Details of [ 3453-33-6 ]

CAS No. :3453-33-6
Formula : C12H10O2
M.W : 186.21
SMILES Code : C1=C(C=O)C=CC2=C1C=CC(=C2)OC
MDL No. :MFCD00081152
InChI Key :VZBLASFLFFMMCM-UHFFFAOYSA-N
Pubchem ID :76991

Safety of [ 3453-33-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 3453-33-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3453-33-6 ]

[ 3453-33-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 3453-33-6 ]
  • [ 2605-68-7 ]
  • [ 178552-34-6 ]
YieldReaction ConditionsOperation in experiment
In xylenes; at 170℃; for 4h;Heating / reflux; EXAMPLE 7; To a xylenes solution of 6-methoxy-2-naphthaldehyde (0.855g, 4.585 mmol) was added the stabilized ylide shown in Scheme 2 (2.16g, 5.96 mmol, 1.3 eq.) at room temperature. The solution was heated to reflux for 4 h. The solvent was removed under vacuum, and the residue was chromatographed with AcOEt/Hexanes (4 to 1) to obtain the ethyl enoate intermediate. To a methanol solution of this intermediate (5.73 g) was added Pd/C (0-3 g), and the mixture was subjected to <n="33"/>hydrogenation under a balloon atmosphere of H2 gas, at room temperature for 16 h. The solution was filtered, and the solvent was removed in vacuo to obtain the saturated ester. The methoxy naphthyl ester (5.73 g) was treated with NCS (0.82g, 6.11 mmol, 1.1 eq) in DMF solvent at room temperature, and the solution was stirred for 16 h. Removal of the DMF in vacuo provided a residue which was recrystalized from methanol/methylene chloride to obtain the chlorinated intermediate. The racemic mixture of this chloride (1.5 g, 3.69 mmol) was separated into its single enantiomers using chiral HPLC with a Chiralcel OJ column, and isocratic elution with 35% isopropanol-heptane. The ethyl ester intermediate (65 mg, 0.21 mmol) was dissolved in (1:1) acetic acid-HCl (2 mL) and heated to 110 0C for 10 min. Then 5 mL of water was added, and the solution cooled to 0 0C to obtain the acid intermediate after filtration. Oxalyl chloride (0.3 mmol) was then added to a CH2CI2 (2 mL) solution of this acid intermediate (45 mg, 0.1 mmol), and one drop of DMF was added at 0 0C. The solvent was removed in vacuo after the solution was sirred for 1 h at room temperature. The residue was dissolved in THF (2 mL), and this solution was added to a THF (2 mL) solution of 3-amino-2-carboxylthiophene (0.11 mmol) and Et3N (0.3 mmol) at 0 0C. The pure thiophene methyl ester intermediate was obtained after HPLC purification. Potassium trimethylsilanolate (4 eq, 0.4 mmol) was added to a THF solution of this methyl ester intermediate (0.09 mmol) at 0 0C. The solution was stirred at room temperature for 2 h, and the desired product was obtained by preparative RPHPLC purification. 1H NMR (CD3OD, 500 MHz) δ 8.07 (d, IH), 7.99 (d, IH), 7.74 (d,lH), 7.66 (s, IH), 7.64(d, IH), 7.47 (dd IH), 7.40(d, IH), 4.00 (s, 3H), 3.17(m, IH), 2.97 (m, 2H), 1.30 (d, 3H); LCMS m/z 402 (M-I).
 

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