Acetic Anhydride → HCID 15070135, compound

HRID 2081317Notes

Reaction equation

HRID 2081317 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]/[CH:17]=[CH:18]/[CH:19]([OH:28])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:2].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:15]=[CH:16]/[CH:17]=[CH:18]/[CH:19]([O:28][C:30](=[O:32])[CH3:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15070124HCID 15070124, compound

Product 1

HCID 15070135HCID 15070135, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 60 mg of 4-[2-[(1E,3E)-(5RS)-5-hydroxy-1,3-tridecadienyl]-phenoxy]-butyric acid ethyl ester in 0.5 ml of pyridine is mixed with ice cooling and under argon atmosphere with 0.12 ml of acetic anhydride and stirred for 4 hours at room temperature. The reaction mixture is concentrated by evaporation and the residue is chromatographed on silica gel with n-hexane/ethyl acetate=95/5. 42 mg of 4-[2-[(1E,3E)-(5RS)-5-acetoxy-1,3-tridecadienyl]-phenoxy]-butyric acid ethyl ester is obtained as a colorless oil.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is chromatographed on silica gel with n-hexane/ethyl acetate=95/5

Sources & evidence

ORD record
ord-6480a4bb3bb44b55889f8bc1136c4aae
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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