Diethyl Ether → HCID 67050187, compound

HRID 2103801Notes

Reaction equation

HRID 2103801 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-5ddb3bbe931b43efb1d275a80a6e2ecb
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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