Triphenylphosphine → 1-(1-Methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester

HRID 1889266Notes

Reaction equation

HRID 1889266 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:15])=[O:4].[O:16]([CH2:23][CH:24](O)[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH:24]([CH3:25])[CH2:23][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 928391-Phenoxy-2-propanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 688408431-(1-Methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.00 g 1-hydroxy-naphthalene-2-carboxylic acid methyl ester, 0.75 g 1-phenoxy-propan-2-ol and 3.89 g triphenyl phosphine in 60 ml dry THF at 0° C. 3.00 g diisopropylazodicarboxylate were added. After 48 h at room temperature the reaction was concentrated in vacuo, the residue was taken up in ethyl acetate, washed with sat. sodium hydrogen carbonate solution and dryed over magnesium sulphate. The solvent was removed in vacuo and after chromatography on silica (ethyl acetate/heptane) 0.47 g 1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester were obtained.

Workup

  1. customat 0° C
  2. concentrationAfter 48 h at room temperature the reaction was concentrated in vacuo
  3. washwashed with sat. sodium hydrogen carbonate solution
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-babc16f628ae4cf982e714f4b1b78abd
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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