Trifluoroacetic acid → Methyl (2-oxo-3-benzyl-5-methyl-cyclohept-4-en-1-yl)-ethanoate

HRID 1755807Notes

Reaction equation

HRID 1755807 reaction equation
C(OC([C:8]1([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:14][CH2:13][C:12]([CH3:15])=[CH:11][CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[O:23]=[C:9]1[CH:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[C:12]([CH3:15])[CH2:13][CH2:14][CH:8]1[CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57015558Methyl (1-t-butyloxycarbonyl-2-oxo-3-benzyl-5-methyl-cyclohept-4-en-1-yl)-ethanoate

Product 1

HCID 56988104Methyl (2-oxo-3-benzyl-5-methyl-cyclohept-4-en-1-yl)-ethanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the above di-ester (22) (1.35 g) in CH2Cl2 (20 mL) was added trifluoroacetic acid (80 mL). After stirring for 45 min the reaction was evaporated to dryness and re-evaporated twice with fresh toluene to remove any residual TFA. The oil which remained was then taken up in toluene (100 mL) and refluxed under Ar for 1 h. The product (23) was obtained after evaporation and purification by flash chromatography on silica gel eluted with 10% ethyl acetate in n-hexane (0.85 g, 85%).

Workup

  1. customwas evaporated to dryness
  2. customre-evaporated twice with fresh toluene
  3. customto remove any residual TFA
  4. temperaturerefluxed under Ar for 1 h

Sources & evidence

ORD record
ord-d6472122aa2e46d6a12ebdbcc9e8661d
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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