Hydrochloric Acid → HCID 12165901, compound

HRID 2426976Notes

Reaction equation

HRID 2426976 reaction equation
[OH:1][CH2:2][C:3](=[CH2:7])[C:4]([OH:6])=[O:5].[Si:8](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1[CH:30]=[CH:29]N=C1.Cl>CN(C=O)C>[Si:8]([O:1][CH2:2][C:3](=[CH2:7])[C:4]([O:6][CH2:29][CH3:30])=[O:5])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 1995342-(Hydroxymethyl)-2-propenoic acid

Product 1

HCID 12165901HCID 12165901, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(hydroxymethyl)acrylic acid (520 mg) in DMF (5.0 mL) were added tert-butyldiphenylsilyl chloride (1.65 g) and imidazole (680 mg) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuum condition. The obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1→9:1) to give the title compound (1.35 g) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuum condition
  5. customThe obtained residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1→9:1)

Sources & evidence

ORD record
ord-07b8ff957d3740e9b931cec28339750b
Source dataset
uspto-grants-2011_06
Patent number
US07968572B2

Reaction notes

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