Trifluoroacetic acid → HCID 68089112, compound

HRID 1918231Notes

Reaction equation

HRID 1918231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:14])=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.CO[CH2:17][N:18]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19][Si](C)(C)C.C(O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl>[CH3:13][O:12][C:10]([CH:9]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)([CH3:14])[CH2:17][N:18]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:19]1)=[O:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11356281HCID 11356281, compound

Product 1

HCID 68089112HCID 68089112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 11.7 g (55 5 mmol) (E)-methyl 3-(4-chlorophenyl)but-2-enoate (Organic Letters 2008, 2131-2134), 16.5 g (69 4 mmol) N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine and 0.63 g (5.5 mmol) TFA in 30 mL DCM was stirred at 0-5° C. for 1 h and then at room temperature over night. The mixture was neutralised with NEt3 and evaporated. The residue was taken up on isolute and purified by column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. After evaporation of the product containing fractions 9.6 g (50%) of the title compounds was isolated as colorless oil. MS m/e: 344.1 [M+H]+.

Workup

  1. waitat room temperature over night
  2. customevaporated
  3. custompurified by column chromatography on silica eluting with a gradient
  4. customformed from ethyl acetate and heptane
  5. customAfter evaporation of the product
  6. additioncontaining fractions 9.6 g (50%) of the title compounds
  7. customwas isolated as colorless oil

Sources & evidence

ORD record
ord-cb8003ce4a14489e9d5e5329887ed12d
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

Loading…