Hydrochloric Acid → HCID 68495141, compound

HRID 1616619Notes

Reaction equation

HRID 1616619 reaction equation
C(NC(C)C)(C)C.[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:17]#[C:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[C:14]([OH:16])[CH:15]=1.[CH3:23][Si:24]([CH3:31])([CH3:30])[CH2:25][CH2:26][O:27][CH2:28]Cl.Cl>C(Cl)Cl.O>[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:17]#[C:18][Si:19]([CH3:20])([CH3:22])[CH3:21])=[C:14]([O:16][CH2:28][O:27][CH2:26][CH2:25][Si:24]([CH3:31])([CH3:30])[CH3:23])[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 684905065-Methoxy-2-[2-(trimethylsilyl)ethynyl]phenol

Product 1

HCID 68495141HCID 68495141, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add diisopropylamine (11.0 mL, 78.3 mmol) to a rapidly stirred solution of 5-methoxy-2-trimethylsilanylethynyl-phenol (11.5 g, 52.2 mmol) in CH2Cl2 at room temperature under N2. Add 2-(trimethylsilyl)ethoxymethyl chloride (13.9 mL, 78.3 mmol) dropwise over 5 minutes and stir at room temperature under N2 overnight Acidify with aqueous 1N HCl solution, add water, separate layers. Extract from aqueous layer with CH2Cl2 (×2), dry combined organic layers over MgSO4 and concentrate. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes to afford 4-methoxy-2-(2-trimethylsilanyl-ethoxymethoxy)-1-trimethylsilanylethynyl-benzene (13.5 g, 74%). MS (IS) 351 (M+1)+.

Workup

  1. customseparate layers
  2. extractionExtract from aqueous layer with CH2Cl2 (×2)
  3. dry with materialdry combined organic layers over MgSO4
  4. concentrationconcentrate
  5. custompurify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes

Sources & evidence

ORD record
ord-2bcbed83868a485b8a6ee7719b0ee723
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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