Triethylamine → 1-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)ethane

HRID 1588127Notes

Reaction equation

HRID 1588127 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:4]=1[CH2:19][CH:20]=O.[CH3:22][C:23]1([CH3:31])[O:30][C:28](=[O:29])[CH2:27][C:25](=[O:26])[O:24]1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][O:11][CH3:12])=[CH:7][C:6]([O:13][CH3:14])=[C:5]([O:15][CH2:16][O:17][CH3:18])[C:4]=1[CH2:19][CH:20]=[C:27]1[C:28](=[O:29])[O:30][C:23]([CH3:31])([CH3:22])[O:24][C:25]1=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 197572302-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehyde

Product 1

HCID 197571651-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)ethane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2.7 Grams (9.0 mM) of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]acetoaldehyde was dissolved in 80 ml of benzene, then to this solution was added 1.56 g (10.8 mM) of Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) and 2.18 g (21.6 mM) of triethylamine were added and the reaction mixture was stirred at room temperature for 12 hours. 100 Milliliters of benzene was added to the reaction mixture and washed twice with 200 ml of water and further washed twice with a saturated sodium chloride aqueous solution, then the benzene solution was dried over anhydrous magnesium sulfate. The benzene solution was concentrated under reduced pressure and the residue obtained was purified by a silica gel column chromatography (diameter 5 cm×length 15 cm, eluent: 30% ethyl acetatehexane, "Wakogel C-200") to yield 2.9 g of 1-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)ethane. Light yellow indefinite form powdery substance.

Workup

  1. additionwere added
  2. washwashed twice with 200 ml of water
  3. washfurther washed twice with a saturated sodium chloride aqueous solution
  4. dry with materialthe benzene solution was dried over anhydrous magnesium sulfate
  5. concentrationThe benzene solution was concentrated under reduced pressure
  6. customthe residue obtained
  7. customwas purified by a silica gel column chromatography (diameter 5 cm×length 15 cm, eluent: 30% ethyl acetatehexane, "Wakogel C-200")

Sources & evidence

ORD record
ord-7ed268b4d2c64e95bd58f109c77cbf37
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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