Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dichlorodimethylsilane | HCID 6398 | — |
| Reactant | Ethyl 4-chlorosulfonyl-2-methylphenoxyacetate | HCID 11415129 | — |
| Reactant | HCID 59674256 | HCID 59674256 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58629923 | HCID 58629923 | 50.2% |
Reaction Steps
Zinc (229 mg, 3.50 mmol) was added to EtOAc (10 mL) followed by AcOH (115 μM, 2.00 mmol) and ethyl [4-(chlorosulfonyl)-2-methylphenoxy]acetate (293 mg, 1.00 mmol). After 2 hours, dichlorodimethylsilane (258 mg, 2.00 mmol) was added followed by 1-[4′-(trifluoromethyl)-3-biphenylyl]ethanol (266 mg, 1.00 mmol) and the mixture stirred for a further 1 hour and then heated at 80° C. for 5 hours. The mixture was then cooled, diluted with EtOAc and washed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, water and brine, and then reduced. Purification by Biotage™ chromatography (silica) eluting with petrol:EtOAc (9:1) afforded the title compound as a colourless oil (238 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07338960B2 |
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| Source dataset | uspto-grants-2008_03 |
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| ORD ID | ord-79411b63286245e3acdd06f653a78483 |
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| Source note | uspto-grants-2008_03 |
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