2-Nitropropane → HCID 86662038, compound

HRID 591850Notes

Reaction equation

HRID 591850 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:6][CH2:7][CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].[N+](C(C)C)([O-])=[O:22].[O-]CC.[Na+]>C(OCC)(=O)C>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][CH2:8][CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:19]=[C:18]([CH3:20])[CH:17]=1)[CH:2]=[O:22])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 2723922Sodium ethoxideHCID 66675147HCID 66675147, compound

Product 1

HCID 86662038HCID 86662038, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of [2-(3-bromomethyl-5-methyl-phenoxy)-ethoxy]-tert-butyl-dimethyl-silane (2.17 g, 6.04 mmol) under nitrogen in 2-nitropropane (2.0 mL, 20 mmol) was added sodium ethoxide (0.620 g, 9.06 mmol). The resulting mixture was heated at 90° C. for 15 hours, and was then diluted with ethyl acetate and quenched with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate and the combined organic layers were backwashed with water and brine, dried over sodium sulfate, and concentrated. The crude material (1.81 g) was purified by column chromatography (silica gel 230-400 mesh; 1/0 to 4/1 hexanes/EtOAc as eluent) to give 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-methyl-benzaldehyde as a yellow oil. Yield: 0.97 g (55%).

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude material (1.81 g) was purified by column chromatography (silica gel 230-400 mesh; 1/0 to 4/1 hexanes/EtOAc as eluent)

Sources & evidence

ORD record
ord-24109cbe8e0d4bf9b6222eb7cf3fdd5c
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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