Methylparaben → HCID 10587638, compound

HRID 1386973Notes

Reaction equation

HRID 1386973 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.O[CH2:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[N:35]1([CH2:34][CH2:33][CH2:32][O:20][C:21]2[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 2093421-PyrrolidinepropanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 10587638HCID 10587638, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.25 g (23.8 mmol) of triphenylphosphine, 3.30 g (21.7 mmol) of methyl 4-hydroxybenzoate, and 2.80 g (21.7 mmol) of 1-(3-hydroxypropyl)pyrrolidine in 100 mL of CH2Cl2 was treated with 3.80 mL (24.1 mmol) of diethyl azodicarboxylate in a dropwise manner. The reaction was stirred at ambient temperature for 16 h and was quenched by the addition of 20 mL of brine. The two layers were separated, and the organic layer was dried over K2CO3 and concentrated to give 6.10 g of an oily solid which was purified by flash chromatography (SiO2; 0-5% MeOH in CH2Cl2) to afford 2.46 g (9.34 mmol; 43%) of the desired product.

Workup

  1. customwas quenched by the addition of 20 mL of brine
  2. customThe two layers were separated
  3. dry with materialthe organic layer was dried over K2CO3
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40a7e72c46f34009b56d14b81be8eaba
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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