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Methyl vinyl ketone → HCID 70873097, compound

HRID 1844718
Notes
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Reaction equation

HRID 1844718 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:26][C:27](=[O:30])[CH:28]=[CH2:29]>CCO.[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[C:13]([C:11]1[CH:10]=[C:7]([C:8](=[O:9])[CH2:29][CH2:28][C:27](=[O:30])[CH3:26])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 81531DiisopropylethylamineHCID 12682533,5-Bis(tert-butyl)benzaldehyde

Product 1

HCID 70873097HCID 70873097, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideCatalyst
HCID 702
Ethanol
Solvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of 3,5-di-tert-butylbenzaldehyde (10.9 g, 50 mmol) in EtOH (200 mL) was added DIPEA (12.9 g, 100 mmol), but-3-en-2-one (3.5 g, 50 mmol) and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (2.5 g, 10 mmol). This mixture was heated to 75-80° C. overnight, evaporated, diluted with water (50 mL) and extracted with EA. The organic layer was washed with brine, dried, concentrated and purified by CC (EA/PE=1/100) to afford compound 5a (6.4 g, 44%) as colorless oil.

Workup

  1. customevaporated
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EA
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by CC (EA/PE=1/100)

Sources & evidence

ORD record
ord-6abcab52f0874c1fac30f5091aa109f8
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946446B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes