HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butanol → tert-Butyl 2-(4-tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | 2-(4-Tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetic acid | HCID 19385597 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Benzene | HCID 241 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert-Butyl 2-(4-tert-butyldimethylsilyloxymethyl-2-propylphenoxy)-2-phenylacetate | HCID 19385645 | 73.8% |
Reaction Steps
To a solution of 929 mg (2.24 mmol) of the product of Step L in benzene were added oxalyl chloride (234 mL, 2.69 mmol) and one drop of DMF at 0° C. The solution was stirred at rt for 45 minutes. After concentration the residue was dissolved in CH2Cl2 (10 mL). The solution was added to a solution of tert-butyl alcohol (253 mL, 2.69 mmol) and Et3N in CH2Cl2 (10 mL) at 0° C. The solution was stirred at rt for 3 hours. The mixture was poured into EtOAc (50 mL) and washed with H2O (1×) and brine, and dried over anhydrous MgSO4. Concentration gave 778 mg of the title compound as a slightly yellow glass.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05240938 |
| Source dataset | uspto-grants-1993_08 |
| ORD ID | ord-f13c89c6a39a445f93f96a257b6b993a |
| Source note | uspto-grants-1993_08 |