Water → HCID 67244725, compound

HRID 2425532Notes

Reaction equation

HRID 2425532 reaction equation
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Br:36])(=[O:19])[CH3:18].O>C1(C)C=CC=CC=1.FC(F)(F)C(O)=O>[C:17]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[C@H:28]1[C@H:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[Br:36])[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:14]1)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 44139027Phenol, 2-[(1E)-2-(2-bromophenyl)ethenyl]-4-chloro-, 1-acetate

Product 1

HCID 67244725HCID 67244725, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 1140TolueneSolvent

Procedure

N-benzyl-N-methoxymethyl-N-(trimethylsilylmethyl)amine (5.0 g, 21.06 mmol) was added dropwise with a syringe over 30 minutes to a suspension of (E)-2-(2-bromostyryl)-4-chlorophenyl acetate (Example 1; 7.0 g, 19.9 mmol) in toluene (25 ml) containing trifluoroacetic acid (3 drops) while stirring at room temperature. After additional stirring for one hour water (10 ml) was added. The toluene layer was separated. The aqueous layer was extracted with toluene (25 ml). The combined organic layers were dried with Na2SO4 and evaporated under vacuum to give the crude cycloadduct as a clear and colorless oil, 10.76 g (>100%) in quantitative yield.

Workup

  1. additionwas added
  2. customThe toluene layer was separated
  3. extractionThe aqueous layer was extracted with toluene (25 ml)
  4. dry with materialThe combined organic layers were dried with Na2SO4
  5. customevaporated under vacuum
  6. customto give the crude cycloadduct as a clear and colorless oil, 10.76 g (>100%) in quantitative yield

Sources & evidence

ORD record
ord-e6441431342a4e2ab9d9546a6e317f4d
Source dataset
uspto-grants-2011_06
Patent number
US07964739B2

Reaction notes

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