Ethylparaben → HCID 22729995, compound

HRID 1785803Notes

Reaction equation

HRID 1785803 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C:33]1[CH:43]=[CH:42][C:36]([C:37]([O:39][CH2:40]C)=[O:38])=[CH:35][CH:34]=1.[CH2:44]([C:48]1[CH:55]=[CH:54][C:51]([CH2:52]O)=[CH:50][CH:49]=1)[CH2:45][CH2:46][CH3:47]>C1COCC1>[CH2:44]([C:48]1[CH:49]=[CH:50][C:51]([CH2:52][O:32][C:33]2[CH:43]=[CH:42][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)=[CH:54][CH:55]=1)[CH2:45][CH2:46][CH3:47]

Participants

6

Reactant 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5782884-Butylbenzyl alcohol

Product 1

HCID 22729995HCID 22729995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of triphenylphosphine (656 mg, 2.50 mmol) in THF (12 mL) at 0° C. was treated with diethyl azodicarboxylate (442 mg, 2.54 mmol), stirred for 20 minutes, treated with ethyl 4-hydroxybenzoate (350 mg, 2.30 mmol) and 4-butylbenzyl alcohol (414 mg, 2.52 mmol), warmed to room temperature, stirred for 16 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product.

Workup

  1. stirringstirred for 16 hours
  2. concentrationconcentrated
  3. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-16643f6d83bf4543a8446ff6fecc126f
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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