Water → HCID 69541297, compound

HRID 1370757Notes

Reaction equation

HRID 1370757 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:15])=[C:6]([O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=1.[CH2:16]1[CH2:26]CN2C(=NCCC2)C[CH2:17]1.BrC(C)C.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH:16]([CH3:26])[CH3:17])=[C:6]([O:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:12])[CH3:13])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21130787HCID 21130787, compound

Product 1

HCID 69541297HCID 69541297, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

2,2-dimethylpropionic acid 5-bromo-2-hydroxyphenylester (500 mg) was dissolved in dimethylformamide and stirred with 1,8-diazabicyclo[5.4.0]undece-7-ene (DBU; 0.32 ml) for 10 minutes. Then, 2-bromopropane (0.25 ml) was added and heated at 40° C. After the reaction was completed, water was added to dilute and extracted with ethylacetate. An organic layer was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The residue was separated through a silica gel attributed chromatography (an eluting agent: ethylacetate/n-hexane=1/12, v/v). As a result, the present compound (340 mg, productive yield 60%) was obtained.

Workup

  1. additionto dilute
  2. extractionextracted with ethylacetate
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationdistilled under reduced pressure
  6. customThe residue was separated through a silica gel
  7. customAs a result, the present compound (340 mg, productive yield 60%) was obtained

Sources & evidence

ORD record
ord-265334f259c8497893fde6335815ab56
Source dataset
uspto-grants-2003_06
Patent number
US06583321B1

Reaction notes

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