Diethyl Ether → HCID 67050187, compound

HRID 1881533Notes

Reaction equation

HRID 1881533 reaction equation
[CH2:1](OCC)C.C[Mg]Br.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([CH:28]=[O:29])[C:23]=2[O:24][CH2:25][O:26][CH3:27])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+]>C1COCC1>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[C:22]([CH:28]([OH:29])[CH3:1])[C:23]=2[O:24][CH2:25][O:26][CH3:27])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 86604735HCID 86604735, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67050187HCID 67050187, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 M Ethyl ether solution (2.0 mL, 6.0 mmol) of methylmagnesium bromide was added dropwise to 2-(4-t-butylphenyl)-3-methoxymethyloxy-4-formylthiophene (0.77 g, 2.5 mmol) in THF (2.5 mL) under cooling with ice, and the reaction solution was stirred for 1 hour under cooling with ice. After addition of saturated aqueous ammonium chloride, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1) to give the desired product as a pale yellow oil (0.64 g, yield 80%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-7217a3c1d537409f9122f43104587584
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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