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Diethyl Ether → HCID 67050265, compound

HRID 2103815
Notes
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Reaction equation

HRID 2103815 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:20]=[O:21])[C:15]=2[O:16][CH2:17][O:18][CH3:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)C.[CH:27]([Mg]Br)([CH3:29])[CH3:28].[Cl-].[NH4+]>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([CH:20]([OH:21])[CH:27]([CH3:29])[CH3:28])[C:15]=2[O:16][CH2:17][O:18][CH3:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 86604735HCID 86604735, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 67050265HCID 67050265, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 2-(4-t-butylphenyl)-3-methoxymethyloxy-4-formylthiophene (3.0 g, 10 mmol) in THF (2.5 mL), 2.0 M ethyl ether solution (6.0 mL, 12 mmol) of isopropylmagnesium bromide was added dropwise under cooling with ice, followed by stirring for 2.5 hours under cooling with ice. A saturated ammonium chloride aqueous solution was added to the reaction solution, and then extraction was carried out with ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous sodium sulfate. The obtained organic layer was concentrated, and then purification was carried out with a silica gel column chromatography (n-hexane/ethyl acetate=3/1) to obtain the desired product as a pale yellow oil (1.18 g, yield 34%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionextraction
  4. washthe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe obtained organic layer was concentrated
  7. custompurification

Sources & evidence

ORD record
ord-aef1b30292614c09916d3368203ba676
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576115B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes