Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid methyl ester

HRID 1651250Notes

Reaction equation

HRID 1651250 reaction equation
[CH2:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH3:16])=[CH:7][C:6]=1[CH:17]=O)[CH2:2][CH2:3][CH3:4].[C:19]([CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH3:22])=[O:20]>ClCCl>[CH3:22][O:21][C:19](=[O:20])/[CH:23]=[CH:17]/[C:6]1[CH:7]=[C:8]([O:15][CH3:16])[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 147427681-Butyl-4-methoxy-2-naphthalenecarboxaldehyde

Product 1

HCID 14742787(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 111, 1-butyl-4-methoxy-2-naphthalenecarboxaldehyde (4.05 g) and (carbomethoxymethylene)triphenylphosphorane (6 g) in dichloromethane (40 mL) was stirred at room temperature for 42 hours. Crystallization of the crude reaction product from the normal work up gave 4.1 g of (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid methyl ester, mp 63°-64° C. Anal. Calcd for C19H22O3 : C, 76.48; H, 7.43 Found: C, 75.89; H, 7.26

Workup

  1. customCrystallization of the crude
  2. customreaction product from the normal work up gave 4.1 g of (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid methyl ester, mp 63°-64° C

Sources & evidence

ORD record
ord-f5995f1232b84a16bca3dc8e61b3b5f7
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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