Dimethyl malonate → HCID 11482150, compound

HRID 1385546Notes

Reaction equation

HRID 1385546 reaction equation
[CH2:1]([C:6]1[CH:7]([OH:11])[CH2:8][CH2:9][CH:10]=1)/[CH:2]=[CH:3]\[CH2:4][CH3:5].[C:12](OC)(=[O:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15]>>[C:14]([O:16][CH3:17])(=[O:15])[CH2:13][C:12]([O:11][C@@H:7]1[CH2:8][CH2:9][CH:10]=[C:6]1[CH2:1]/[CH:2]=[CH:3]\[CH2:4][CH3:5])=[O:18]

Participants

3

Reactant 2

HCID 7943Dimethyl malonateHCID 11469172HCID 11469172, compound

Product 1

HCID 11482150HCID 11482150, compound

Procedure

A mixture of (Z)-2-(2-pentenyl)-2-cyclopenten-1-ol (17.8 g; 117 mmol), dimethyl malonate (17.8 g; 135 mmol), ground KHCO3 (0.58 g; 5.8 mmol) and Novozym 435® (immobilized Candida antarctica from Novo Nordisk; 1.80 g) was gently swirled in a 100 ml flask connected to a Büchi rotavapor at 40° C. and 10 hPa. After 80 min., the reaction mixture was filtered, washed (sat. aq. NaHCO3, sat. aq. NaCl), dried (Na2SO4) and concentrated (30.8 g). Bulb-to-bulb distillation afforded 15.5 g of volatiles (oven temp. 70° C./10-0.1 hPa) and ca. 11.14 g (95% pure, 36%, 97% ee) of the desired product which is isolated at an oven temperature of 80-130° C./0.06 hPa.

Workup

  1. customwas gently swirled in a 100 ml flask
  2. customconnected to a Büchi rotavapor at 40° C.
  3. filtrationthe reaction mixture was filtered
  4. washwashed (sat. aq. NaHCO3, sat. aq. NaCl)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated (30.8 g)
  7. distillationBulb-to-bulb distillation

Sources & evidence

ORD record
ord-c8859b1276c44d90ac745842692e3a1e
Source dataset
uspto-grants-2001_07
Patent number
US06262288B1

Reaction notes

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