Toluene → HCID 67294316, compound

HRID 2061550Notes

Reaction equation

HRID 2061550 reaction equation
[F:1][C:2]1C=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[N+:12]([O-])[C:11]([CH3:15])=[C:10]3[O:16][C:17]([CH3:21])([CH3:20])[O:18][CH2:19][C:9]=23)=[O:7])=[CH:4][CH:3]=1.CC[O:26]C(C)=O.C1(C)C=CC=CC=1.Cl[CH2:38][Cl:39]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[Cl:39][C:38]1[CH:22]=[C:5]([C:6]([C:8]2[CH:13]=[N:12][C:11]([CH2:15][OH:26])=[C:10]3[O:16][C:17]([CH3:21])([CH3:20])[O:18][CH2:19][C:9]=23)=[O:7])[CH:4]=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 67300315HCID 67300315, compound

Product 1

HCID 67294316HCID 67294316, compound

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent2×

Procedure

5.5 g of 5-(4-fluorobenzoyl)-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine 7-oxide was dissolved in 20 mL dichloromethane (DCM) in 5 mL of Trifluoroacetic anhydride (TFAA) followed by vigorous boiling. When the boiling subsided an additional 30 mL of TFAA was added and the solution was stirred overnight (14 h). TLC revealed completion of the reaction (Rf EtOAc; (s.m. 0.2), product 0.9). The DCM was removed by evaporation and the solvent switched to MeOH (100 mL). This solution was stirred for 30 min after which evaporation affording thick oil. Toluene was added and removed under high vacuum yielding a foam containing the desired product (1d).

Workup

  1. additionwas added
  2. customThe DCM was removed by evaporation
  3. stirringThis solution was stirred for 30 min
  4. customafter which evaporation
  5. customaffording thick oil
  6. customremoved under high vacuum
  7. customyielding a foam

Sources & evidence

ORD record
ord-156e6b1505a7473db46383111fe0ba3c
Source dataset
uspto-grants-2012_10
Patent number
US08283366B2

Reaction notes

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