Benzoic Acid → HCID 14484451, compound

HRID 1586901Notes

Reaction equation

HRID 1586901 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][C@@H:33]1[CH2:38][CH:37]=[CH:36][CH2:35][C@H:34]1[C:39]([O:41][CH2:42][CH3:43])=[O:40].[C:44](O)(=[O:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1COCC1>[C:44]([O:32][C@H:33]1[CH2:38][CH:37]=[CH:36][CH2:35][C@H:34]1[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14484449HCID 14484449, compound

Product 1

HCID 14484451HCID 14484451, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (2.06 g, 11.8 mmol) was added dropwise to a solution of triphenylphosphine (3.08 g, 11.8 mmol) in THF (35 ml) at 0° C. over a period of 5 min. Trans 1-Hydroxy-2-carboethoxycyclohex-4-ene 2a (1.00 g, 5.88 mmol in 5 ml THF) was then added slowly, the mixture was stirred for 5 min, and then benzoic acid (1.44 g, 11.8 mmol, in 5 ml THF) was added. The mixture was stirred at RT for 2 hours. Solvents were evaporated, an the residue purified by chromatography on silica gel (EtOAc:hexane 2:8 as eluant). The product was then distilled under vacuum to yield ethyl cis-2-benzoyloxy-cyclohex-4-enecarboxylate (4, 1.1 g, 71%).

Workup

  1. stirringThe mixture was stirred at RT for 2 hours
  2. customSolvents were evaporated
  3. customan the residue purified by chromatography on silica gel (EtOAc:hexane 2:8 as eluant)
  4. distillationThe product was then distilled under vacuum

Sources & evidence

ORD record
ord-bed4d31c16884f9982c3c1ef4bc1198f
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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