Trifluoroacetic acid → HCID 68089270, compound

HRID 1918225Notes

Reaction equation

HRID 1918225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[CH3:14])/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.CO[CH2:24][N:25]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:26][Si](C)(C)C.CCN(CC)CC>C(Cl)Cl>[CH3:13][O:12][C:10]([C:9]1([CH3:14])[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:24][N:25]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:26]1)=[O:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11264298HCID 11264298, compound

Product 1

HCID 68089270HCID 68089270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 8.8 g (41.8 mmol) (E)-methyl 3-(4-chlorophenyl)-2-methylacrylate (freshly distilled) 0.476 g (4.18 mmol) TFA, and 12.4 g (52 2 mmol) N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine in 100 mL DCM was stirred at 0-5° C. for 1 h and at room temperature. NEt3 was added and the mixture was concentrated. The residue was purified by column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product containing fractions 7.55 g (53%) of the title compound as colorless oil. MS m/e: 344.1 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified by column chromatography on silica eluting with a gradient
  3. customformed from ethyl acetate and heptane
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions 7.55 g (53%) of the title compound as colorless oil

Sources & evidence

ORD record
ord-6ec7d09db5f2403aa5e6f6caecdfb4d9
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

Loading…