Trifluoroacetic acid → HCID 57496390, compound

HRID 537743Notes

Reaction equation

HRID 537743 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]1(=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])/[CH2:18][CH2:19][CH2:20][C:21]2[C:26]/1=[CH:25][CH:24]=[CH:23][CH:22]=2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]2([C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 12322843HCID 12322843, compound

Product 1

HCID 57496390HCID 57496390, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (2.112 ml, 8.26 mmol) and ethyl(2E)-3,4-dihydronaphthalen-1(2H)-ylideneacetate (1.785 g, 8.26 mmol) in CH2Cl2 (33.3 ml) at 0° C. was added TFA (0.064 ml, 0.826 mmol) dropwise. Removed the ice bath and stirred at room temperature for 4 hours. Dilute with CH2Cl2 and wash twice with saturated NaHCO3. The organics were dried over sodium sulfate, concentrated, and purified on silica gel 20% EtOAc/Hex.

Workup

  1. customRemoved the ice bath
  2. additionDilute with CH2Cl2
  3. washwash twice with saturated NaHCO3
  4. dry with materialThe organics were dried over sodium sulfate
  5. concentrationconcentrated
  6. custompurified on silica gel 20% EtOAc/Hex

Sources & evidence

ORD record
ord-ed29bcbb8dbd4fa2bbd1fb887f112ef2
Source dataset
uspto-grants-2014_10
Patent number
US08865701B2

Reaction notes

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