Water → HCID 117760111, compound

HRID 709665Notes

Reaction equation

HRID 709665 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[O:20][CH3:21].N1C=CC=CC=1.O>C1COCC1.[Ti](Cl)(Cl)(Cl)Cl>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[C:5]2[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:9])=[CH:14][C:13]=1[O:20][CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 117760111HCID 117760111, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of titanium (IV) chloride (11.1 g) in THF (50 mL) was added dropwise a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (4.26 g) and 4-fluoro-3-methoxybenzaldehyde (3.08 g) in THF (50 mL) at 0° C., and then a solution of pyridine (4.00 g) in THF (20 mL) was added dropwise. The reaction mixture was stirred for 1 hr, and water was added. The reaction mixture was extracted with ethyl acetate, and the extract was washed with 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (3.20 g) as a yellow solid. This compound was used for the next step without further purification.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extract was washed with 1N hydrochloric acid and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-23a4e8f0b2cd481abc4f28894a319f53
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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