Diisopropyl Ether → HCID 87083563, compound

HRID 1926565Notes

Reaction equation

HRID 1926565 reaction equation
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[CH3:14][C:15]1([CH:23]=O)[C@@H:20]([CH3:21])[CH2:19][CH2:18][C@H:17](C)[CH2:16]1.O(C(C)C)[CH:26](C)C>>[CH3:23][C:15]1([CH3:14])[CH2:16][CH2:17][CH2:18][C@@H:19]([CH3:26])[C@@H:20]1/[CH:21]=[CH:5]/[C:3]([O:2][CH3:1])=[O:4]

Participants

5

Reactant 4

HCID 7914Diisopropyl Ether2×HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 131729727HCID 131729727, compound

Product 1

HCID 87083563HCID 87083563, compoundYield 41%

Procedure

Trimethyl phosphonoacetate (200 g, 1.1 mol) was added dropwise to a suspension of NaH (44 g, 55% in oil, 1.1 mol) in iPr2O (1600 ml). After 2.5 hours, a solution of trans 2,3,6-trimethyl-2-cyclohexanecarbaldehyde [see C. Chapuis, R. Brauchli, Helv. Chim. Acta 1993, 76, 2070.] (91 g, 0.59 mol) in iPr2O (400 ml) was added dropwise. After 18 hours at 20° C., the reaction mixture was poured onto ice and extracted to neutrality with brine, dried (Na2SO4), concentrated and distilled through a 15 cm Vigreux column to afford the pure desired product in 41% yield.

Workup

  1. waitAfter 18 hours at 20° C.
  2. additionthe reaction mixture was poured onto ice
  3. extractionextracted to neutrality with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. distillationdistilled through a 15 cm Vigreux column

Sources & evidence

ORD record
ord-1f38de0f6739486a8ba20c9176e5d001
Source dataset
uspto-grants-2012_05
Patent number
US08183194B2

Reaction notes

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