Heptane → HCID 54426969, compound

HRID 1861694Notes

Reaction equation

HRID 1861694 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[CH3:25][O:26][C:27](=[O:41])[CH:28]([CH2:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][CH:35]=1)[C:29]([O:31][CH3:32])=[O:30].CCCCCCC>C1C=CC=CC=1>[CH3:32][O:31][C:29](=[O:30])[CH:28]([CH2:33][C:34]1[CH:35]=[CH:36][C:37]([O:11][CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:38][CH:39]=1)[C:27]([O:26][CH3:25])=[O:41]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 121412-(Benzyloxy) ethanolHCID 13831TributylphosphineHCID 54350942HCID 54350942, compound

Product 1

HCID 54426969HCID 54426969, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, 2-benzyloxyethanol (30.4 g, 0.2 mol), tributylphosphine (50.4 g, 0.2 mol) and 2-(4-hydroxy-benzyl)-malonic acid dimethyl ester (example 1b) (42.9 g, 0.18 mol) were successively dissolved in dry benzene (1.5 L). Solid azodicarboxylic dipiperidide (ADDP) (40.4 g, 0.2 mol) was added under stirring at 0° C. to the solution. After 10 min, the reaction mixture was brought to room temperature and the stirring was continued for 16 h. Heptane (0.5 L) was added and the precipitate was filtered off. After evaporation of the solvent the product was chromatographed eluting with heptane graduated with ethyl acetate to give 64.0 g (96%) of 2-[4-(2-benzyloxy-ethoxy)-benzyl]-malonic acid dimethyl ester.

Workup

  1. customwas brought to room temperature
  2. waitthe stirring was continued for 16 h
  3. filtrationthe precipitate was filtered off
  4. customAfter evaporation of the solvent the product
  5. customwas chromatographed
  6. washeluting with heptane

Sources & evidence

ORD record
ord-634e0ee0befe415a9d8e19b22ebc6fe5
Source dataset
uspto-grants-2003_03
Patent number
US06534517B2

Reaction notes

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