Water → HCID 68272223, compound

HRID 2170732Notes

Reaction equation

HRID 2170732 reaction equation
[Li+].[Cl-].[Br:3][C:4]1[CH:27]=[CH:26][C:7]([CH2:8][C:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)([C:15](=[O:17])[CH3:16])C(OCC)=O)=[CH:6][CH:5]=1.O>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)[C:15](=[O:17])[CH3:16])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 433294Lithium ChlorideHCID 70976343HCID 70976343, compound

Product 1

HCID 68272223HCID 68272223, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixed liquid containing LiCl (0.175 g, 4 mmol), ethyl 2,2-bis(4-bromobenzyl)-3-oxobutanoate (0.94 g, 2 mmol) and H2O (0.036 mL) in DMF (4 mL) was stirred under heating at 120° C. for 48 hours. The mixed liquid was then cooled to room temperature, water (10 mL) was added, and the resulting mixture was extracted with ethyl acetate. The resulting organic layer was washed with a saturated saline solution and then dried using MgSO4. The organic layer was concentrated under reduced pressure, and then purified using silica gel column chromatography, yielding the title compound (41) in a yield of 52%.

Workup

  1. temperatureThe mixed liquid was then cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with a saturated saline solution
  4. customdried
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. custompurified

Sources & evidence

ORD record
ord-3be31b9f245c4d1ba6df064e677ba663
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

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