Hydrochloric Acid → Methyl 1-(4'-hydroxymethylphenyl)cyclopent-3-ene-1-carboxylate

HRID 1463528Notes

Reaction equation

HRID 1463528 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:21]([O:23][CH3:24])=[O:22])[CH2:18][CH:17]2[CH:19]=[CH2:20])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[OH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:21]([O:23][CH3:24])=[O:22])[CH2:18][CH:17]=[CH:19][CH2:20]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 19090698Methyl 1-(4'-t-butyldimethylsilyloxymethylphenyl)-2-vinylcyclopropane-1-carboxylate

Product 1

HCID 19090695Methyl 1-(4'-hydroxymethylphenyl)cyclopent-3-ene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound of Step 2, above, (1.8 g, 5.23 mmol) in 25 ml THF was added n-Bu4NF (1.5 g, 5.75 mmol), and the resulting solution was stirred at ambient temperature for 3 hours. The mixture was poured into 50 ml 1N HCl and extracted (EtOAc, 4×30 ml). The combined extracts were dried over MgSO4, filtered and concentrated to yield 1.51 g of the title compound as an oil which was used crude in the next step.

Workup

  1. extractionextracted (EtOAc, 4×30 ml)
  2. dry with materialThe combined extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6539d0df347548cca7a4022e08bd4d9c
Source dataset
uspto-grants-1994_04
Patent number
US05300668

Reaction notes

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