Water → HCID 43516604, compound

HRID 1925792Notes

Reaction equation

HRID 1925792 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.CCN(C(C)C)C(C)C.Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].O>C(Cl)Cl>[CH:1]([C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([O:8][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:4]([O:5][CH3:6])[CH:3]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8655SyringaldehydeHCID 60984Methyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 43516604HCID 43516604, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of syringaldehyde (3.0 g, 16.5 mmol) in methylene chloride (33 mL, 0.5 M) was added Hunig's base (5.7 mL, 32.7 mmol) and methyl bromoacetate (1.87 mL, 19.8 mmol), and the mixture was stirred for 15 hours at room temperature, followed by addition of H2O. The reaction mixture was then extracted with chloroform, washed with saturated saline, next dried over magnesium sulfate, and evaporated under diminished pressure. The residue was subjected to silica gel chromatography, and a white solid product (3.895 g, 92.9%) was obtained from an ethyl acetate/hexane eluent (1:1.5 v/v). Recrystallization of a portion of the white solid product from ethyl acetate gave a colorless needle-like crystal (m.p. 100 to 102° C.).

Workup

  1. extractionThe reaction mixture was then extracted with chloroform
  2. washwashed with saturated saline
  3. dry with materialnext dried over magnesium sulfate
  4. customevaporated under diminished pressure

Sources & evidence

ORD record
ord-853cf2c6f1c541d49b21ece0008895a2
Source dataset
uspto-grants-2012_05
Patent number
US08178727B2

Reaction notes

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