Trifluoroacetic acid → HCID 19906402, compound

HRID 2371801Notes

Reaction equation

HRID 2371801 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](/[C:15](/[CH3:40])=[CH:16]/[C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[C:24]2[CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=2[O:38][CH3:39])=[CH:19][CH:18]=1)=[O:14])(C)(C)C>C(Cl)Cl>[C:13](/[C:15](/[CH3:40])=[CH:16]/[C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[CH:22][CH:23]=[C:24]2[CH2:27][C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][C:29]=2[O:38][CH3:39])=[CH:19][CH:18]=1)([OH:14])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19906382HCID 19906382, compound

Product 1

HCID 19906402HCID 19906402, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (25 ml) was added to a 0° C. solution of methyl E-4-[7-[2-(t-butoxycarbonyl)prop-1-enyl]naphth-1-ylmethyl]-3-methoxybenzoate (6.43 g) in methylene chloride (50 ml). After stirring for 4 hours, the solvent was evaporated without heating. The residue was triturated with ether and the colorless solid filtered. The filtrate was concentrated and hexane was added to give another crop of product as a pale yellow solid. The two crops were combined and dried to give methyl E-4-[7-(2-carboxyprop-1-enyl)naphth-1-ylmethyl]-3-methoxybenzoate (4.43 g, 94%); mp 187.0°-187.5° C.; MS(EI), m/e=390(M+.).

Workup

  1. customthe solvent was evaporated
  2. temperaturewithout heating
  3. customThe residue was triturated with ether
  4. filtrationthe colorless solid filtered
  5. concentrationThe filtrate was concentrated
  6. additionhexane was added
  7. customto give another crop of product as a pale yellow solid
  8. customdried

Sources & evidence

ORD record
ord-fd3dda1d609342c8a0a537f6115133e8
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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