Water → HCID 57810541, compound

HRID 2106459Notes

Reaction equation

HRID 2106459 reaction equation
[C:1]([C:4]1[CH:17]=[C:16]([C:18]([CH2:21][CH3:22])=[CH:19][CH3:20])[CH:15]=[CH:14][C:5]=1[O:6][CH2:7][C:8](=[O:13])C(C)(C)C)(=O)[CH3:2].[CH2:23]1[CH2:33]CN2C(=NCCC2)CC1.[OH2:34]>CN(C=O)C>[CH2:33]([O:34][C:8]([C:7]1[O:6][C:5]2[CH:14]=[CH:15][C:16]([C:18]([CH2:21][CH3:22])=[CH:19][CH3:20])=[CH:17][C:4]=2[C:1]=1[CH3:2])=[O:13])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68813220HCID 68813220, compound

Product 1

HCID 57810541HCID 57810541, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 1-[2-acetyl-4-(1-ethyl-propenyl)-phenoxy]-3,3-dimethyl-butan-2-one (4.80 g, 16.5 mmol) in DMF (40 mL) is treated with DBU (2.51 g, 16.5 mmol) and the solution is heated to 140° C. for 2 h. The reaction mixture is cooled down and poured into water (400 mL) and extracted with EtOAc (2×100 mL). The organic layer is dried over Na2SO4, concentrated, purified on column chromatography (5% EtOAc/Hex) to give the title compound as an oil (3.20 g, 71%)

Workup

  1. temperatureThe reaction mixture is cooled down
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on column chromatography (5% EtOAc/Hex)

Sources & evidence

ORD record
ord-2709c4e2dafb433a842e062c90106f39
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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