Tetrahydrofuran → HCID 57709088, compound

HRID 547132Notes

Reaction equation

HRID 547132 reaction equation
[CH2:1]([Mg]Br)[CH3:2].CO[C:7](=[O:24])[C:8]1[CH:13]=[CH:12][C:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[C:10]([O:22][CH3:23])[CH:9]=1.[Cl-].[NH4+].O1CC[CH2:29][CH2:28]1>>[C:18]([Si:15]([CH3:16])([CH3:17])[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([OH:24])([CH2:1][CH3:2])[CH2:28][CH3:29])=[CH:9][C:10]=1[O:22][CH3:23])([CH3:19])([CH3:20])[CH3:21]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 54422404HCID 54422404, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 57709088HCID 57709088, compoundYield 98%

Procedure

Ethylmagnesium bromide (solution in diethyl ether, 25.5 mL, 77.4 mmol) was added to a solution of 4-(t-butyl-dimethyl-silanyloxy)-3-methoxy-benzoic acid methyl ester (Example 176-(1); 7.9 g, 25.5 mmol) in tetrahydrofuran (50 mL) at room temperature, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=10:1) to give the title compound (8.05 g, 98%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane only to hexane

Sources & evidence

ORD record
ord-89b67ab9afa2415d8f4b79ba25c8ecac
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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