1,2-Dimethoxyethane → HCID 20533586, compound

HRID 1759039Notes

Reaction equation

HRID 1759039 reaction equation
[CH2:1]([C:3]1[C:4](=[O:10])[CH2:5][CH2:6][C:7]=1[CH:8]=O)[CH3:2].CO[CH2:13][CH2:14][O:15]C>>[O:15]=[C:14]([CH2:2][CH2:1][CH2:3][CH2:7][CH3:6])/[CH:13]=[CH:8]/[C:7]1[CH2:6][CH2:5][C:4](=[O:10])[C:3]=1[CH2:1][CH3:2]

Participants

3

Reactant 2

HCID 80711,2-DimethoxyethaneHCID 113095442-Ethyl-3-oxocyclopent-1-ene-1-carbaldehyde

Product 1

HCID 20533586HCID 20533586, compoundYield 80%

Procedure

1.7 g (0.035 mole) of a 50% NaH dispersion is transferred into a dry 500 ml 3-neck flask equipped with an addition funnel, overhead stirrer and septum. The NaH was covered with 175 ml of DME and a solution of 10.1 g (0.045 mole) dimethyl (2-oxoheptyl) phosphonate in 12 ml of DME is added dropwise over a 10 minute period. The mixture is stirred for 1 hour at room temperature to form the sodium salt of the phosphonate. A solution of the crude aldehyde 5 supra [from oxidation of 7.0 g (0.05 mole) of the vinyl compound 4] in 25 ml of DME was added over a twenty-minute period, and the mixture was stirred an additional two hours. The reaction was terminated by the addition of 2.5 ml glacial acetic acid followed by 175 ml water. The reaction mixture was extracted with CHCl3, and the combined organic extracts washed with water and dried over sodium sulfate. The CHCl3 was removed under reduced pressure to yield 12.6 g of crude product. This material was chromatographed over silicic acid using ethyl acetate-cyclohexane for elution to give 6.7 g (80%) of a yellow liquid Ic. The spectral characteristics of this compound were similar to Ia and Ib with the ##STR6## group evident in the nmr spectrum, --(CH2)4CH3 at δ0.9.

Workup

  1. customThe reaction was terminated by the addition of 2.5 ml glacial acetic acid
  2. extractionThe reaction mixture was extracted with CHCl3
  3. washthe combined organic extracts washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe CHCl3 was removed under reduced pressure
  6. customto yield 12.6 g of crude product
  7. customThis material was chromatographed over silicic acid
  8. washfor elution

Sources & evidence

ORD record
ord-335c5bc347d34d1cb9b46ef7330a7b8e
Source dataset
uspto-grants-1982_07
Patent number
US04338466

Reaction notes

Loading…