HCID 86747712, compound → HCID 18957438, compound

HRID 2379534Notes

Reaction equation

HRID 2379534 reaction equation
[CH3:1]/[C:2](/[CH2:16][CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH:3]\[CH2:4][CH2:5][S:6][CH2:7][P:8](=[O:15])([O:12]CC)[O:9]CC>C1(C)C=CC=CC=1>[CH3:1]/[C:2](/[CH2:16][CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH:3]\[CH2:4][CH2:5][S:6][CH2:7][P:8](=[O:9])([OH:12])[OH:15]

Participants

3

Reactant 1

HCID 86747712HCID 86747712, compound

Product 1

HCID 18957438HCID 18957438, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diethyl [(E,E)-4,8,12-trimethyl-3,7,11 -tridecatrienyl]thiomethylphosphonate (0.256 g, 0.636 mmol) was deprotected in a similar fashion as that described in Step 2 of Example 2. The reaction mixture was added toluene (3 mL), then evaporated in vacuo. This process was repeated two more times. The final residue was treated with diluted hydrochloride acid (0.1N) at 0° C., then extracted with ethylacetate. The extract was washed with water the three time (3×10 ML). After drying and filtration, filtrate was concentrated in vacuo to give the title compound (0.1 g, 0.29 mmol, 45%) as a gum.

Workup

  1. customevaporated in vacuo
  2. additionThe final residue was treated with diluted hydrochloride acid (0.1N) at 0° C.
  3. extractionextracted with ethylacetate
  4. washThe extract was washed with water the three time (3×10 ML)
  5. customAfter drying
  6. filtrationfiltration, filtrate
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-c681dda1a97c4bdeaf913a6fdcf90dbe
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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