Mesitylene → HCID 18660186, compound
Reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:6]=1[O:7][CH2:8][C@H:9]1[CH2:11][O:10]1)C=C.C(=O)(O)[O-].[Na+].[C:22]1(C)[CH:27]=C(C)C=C(C)[CH:23]=1>>[CH2:27]([C:15]1[C:5]2[O:4][C@@H:9]([CH2:11][OH:10])[CH2:8][O:7][C:6]=2[CH:12]=[C:13]([Cl:16])[CH:14]=1)[CH:22]=[CH2:23]Participants
Procedure
(R)-2-(2-Allyloxy-5-chlorophenoxymethyl)-oxirane (9.2 g, 38 mmole) was dissolved in 500 ml of mesitylene and refluxed under nitrogen for 48 hours. The solvent was then removed in vacuum and replaced with 500 ml of ethanol. Sodium bicarbonate (50 g, 0.60 mole) was added and the mixture stirred at room temperature under nitrogen for 24 hours. The mixture was then filtered and concentrated in vacuum. The solvent was replaced with 500 ml of methylene chloride and the solution was washed with water and with saturated brine, dried over sodium sulfate, filtered and evaporated in vacuum. The residue was column chromatographed on silica gel using chloroform as eluant to give 8.9 g of the title compound as a colorless oil. 1H (CDCl3) singlet, 6.80 δ (1 H); singlet, 6.73 δ (1 H); multiplet, 5.95 δ (1 H); doublet, 5.10 δ (1 H); doublet, 5.05 δ (1 H); multiplet, 4.25 δ (2 H); multiplet, 4.10 δ (1 H); multiplet, 3.85 δ (2 H); multiplet, 3.30 δ (2 H); broad singlet, 2.00 δ (1 H).
Workup
- temperaturerefluxed under nitrogen for 48 hours
- customThe solvent was then removed in vacuum
- filtrationThe mixture was then filtered
- concentrationconcentrated in vacuum
- washthe solution was washed with water and with saturated brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuum
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-02e8a441deed477d8683093f0034e39f
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05962465
Reaction notes
Loading…