Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Toluene-p-sulphonic anhydride | HCID 77773 | — |
| Reactant | (2-{[(Oxan-2-yl)oxy]methyl}phenyl)methanol | HCID 11345082 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 59712110 | HCID 59712110 | 78.7% |
Reaction Steps
A solution of {2-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl}methanol (5.52 g, 24.84 mmol) in CH2Cl2 (100 ml) was cooled to 0° C. and treated with Et3N (6.92 ml, 49.68 mmol) followed by the addition of Ts2O (8.9 g, 27.33 mmol). The reaction stirred at 0° C. for 3.5 hours. The mixture was diluted with sat. NH4Cl and extracted with CH2Cl12 (2×). The combined organic solutions were washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by normal phase chromatography (10% EtOAc/hexanes—20%) to give a light brown oil (7.36 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07371754B2 |
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| Source dataset | uspto-grants-2008_05 |
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| ORD ID | ord-676f11735f084b89b3a25bd26dfc06c5 |
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| Source note | uspto-grants-2008_05 |
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