Dichloromethane → 2-(5-Methoxy-2-nitrophenyl)-1,3-dioxolane

HRID 1802096Notes

Reaction equation

HRID 1802096 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH:8]=[O:9].C[Si](C)(C)[O:16][CH2:17][CH2:18]O[Si](C)(C)C.C(Cl)Cl>FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C([O-])([O-])=O.[K+].[K+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:8]2[O:16][CH2:17][CH2:18][O:9]2)[CH:10]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 818582,2,7,7-Tetramethyl-3,6-dioxa-2,7-disilaoctaneHCID 2303715-Methoxy-2-nitrobenzaldehyde

Product 1

HCID 572490272-(5-Methoxy-2-nitrophenyl)-1,3-dioxolaneYield 99.2%

Reagents, catalysts & solvents 2

HCID 65367Trimethylsilyl triflateCatalystHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
-78 °C

Procedure

5-Methoxy-2-nitro-benzaldehyde (30.00 g, 0.1656 mol) and 1,2-bis-trimethylsilanyloxy-ethane (40.6 mL, 0.166 mol) were placed in a 40 mL vial, followed by Methylene chloride (1000 mL, 20 mol). The reaction mixture was then cooled to −78° C., and trimethylsilyl trifluoromethanesulfonate (1 mL, 0.008 mol) was added dropwise under N2. The reaction mixture was allowed to warm up to at 23° C. for 1 day. A solution of saturated K2CO3 (50 mL) was added to quench the reaction, and organic layer was separated. Removal of solvent gave a oily product, which was treated with ether/hexanes to give a pure solid product (37.0 g, 99%). NMR (MeOD) δ: 8.01 (d, J=9.0 Hz, 1H), 7.29 (d, J=2.8 Hz, 1H), 7.05 (dd, J=8.9, 2.9 Hz, 1H), 6.49 (s, 1H), 4.85 (s, 3H), 3.91 (s, 4H). MS (M+1): 226.10.

Workup

  1. temperatureto warm up to at 23° C. for 1 day
  2. customto quench
  3. customthe reaction, and organic layer
  4. customwas separated
  5. customRemoval of solvent
  6. customgave a oily product, which

Sources & evidence

ORD record
ord-4bac6d469efe4a948ab6cc727b3d952f
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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