Mesitylene → HCID 18546023, compound

HRID 1267246Notes

Reaction equation

HRID 1267246 reaction equation
C([O:4][C:5]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C@@H:9]1[CH2:11][O:10]1)C=C.[C:24]1(C)[CH:29]=C(C)C=C(C)[CH:25]=1>>[CH2:29]([C:15]1[C:5]2[O:4][CH:9]([CH2:11][OH:10])[CH2:8][O:7][C:6]=2[CH:12]=[CH:13][C:14]=1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH:24]=[CH2:25]

Participants

3

Reactant 2

HCID 7947MesityleneHCID 86586533HCID 86586533, compound

Product 1

HCID 18546023HCID 18546023, compound

Procedure

A solution of (2S)-2-{[2-(allyloxy)-4-(benzyloxy)phenoxy]methyl}oxirane (28.5 g, 91.3 mmole) in 1 L of mesitylene was refluxed under nitrogen for 2 days. The solvent was then removed in vacuum and replaced with 500 mL of ethanol. Sodium bicarbonate (25.0 g) was added and the mixture was stirred under nitrogen for 15 hours. The mixture was filtered, the ethanol was removed in vacuum and 500 mL of methylene chloride added. This solution was washed with 500 mL portions of water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuum to a dark oil. This was column chromatographed on silica gel with methylene chloride as eluant to give 15.6 g of the (S)-enantiomer of the title compound as a tan oil. 1H-NMR (CDCl3): multiplet 7.4 δ (5H); doublet 6.7 δ (1H); doublet 6.5 δ (1H); multiplet 6.0 δ (1H); singlet 5.05 δ (2H); multiplet 5.0 δ (2H); multiplet 4.3 δ (2H); doublet of doublets 4.1 δ (1H); doublet of doublets 3.8 δ (2H); multiplet 3.5 δ (2H), broad singlet 1.9 δ (1H).

Workup

  1. customThe solvent was then removed in vacuum
  2. additionSodium bicarbonate (25.0 g) was added
  3. filtrationThe mixture was filtered
  4. customthe ethanol was removed in vacuum and 500 mL of methylene chloride
  5. additionadded
  6. washThis solution was washed with 500 mL portions of water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum to a dark oil
  10. customThis was column chromatographed on silica gel with methylene chloride as eluant

Sources & evidence

ORD record
ord-1e428212ff9e4663b15fff2f0701faf2
Source dataset
uspto-grants-2003_04
Patent number
US06552049B2

Reaction notes

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