Hydrochloric Acid → HCID 23393475, compound

HRID 498146Notes

Reaction equation

HRID 498146 reaction equation
Cl.[C:2]([O:5][C:6]([CH3:27])([CH2:13][CH2:14][CH2:15][C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)OCC[O:17]1)[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])(=[O:4])[CH3:3]>C1COCC1>[C:2]([O:5][C:6]([CH3:27])([CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:7][CH2:8][CH:9]=[C:10]([CH3:11])[CH3:12])(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69114812HCID 69114812, compound

Product 1

HCID 23393475HCID 23393475, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.76 ml of HCl (1N) was added slowly to a solution of 1.63 g (4.53 mmol) of 1,5-dimethyl-1-[3-(2-phenyl-1,3-dioxolan-2-yl)propyl]-4-hexenyl acetate obtained under d) in 30 ml of THF. The reaction mixture was stirred at 40° or 4 h, cooled down to room temperature, extracted with ether, washed with a saturated solution of NaCl (3×), dried (Na2SO4), filtered and concentrated. Column chromatography (SiO2, heptane/ether 4:1) yielded 1.34 g (94%) of a slightly yellow oil.

Workup

  1. extractionextracted with ether
  2. washwashed with a saturated solution of NaCl (3×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customColumn chromatography (SiO2, heptane/ether 4:1) yielded 1.34 g (94%) of a slightly yellow oil

Sources & evidence

ORD record
ord-3d73594ee54249dfa8dcc6ab00762e4b
Source dataset
uspto-grants-2005_09
Patent number
US06949680B2

Reaction notes

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