HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl Sulfoxide → Ethyl 4-(N-BOC-4-piperidyl)trans-crotonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester | HCID 70670 | — |
| Reactant | 1-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine | HCID 854140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl 4-(N-BOC-4-piperidyl)trans-crotonate | HCID 10017534 | 54.8% |
Reaction Steps
To a stirred solution of oxalyl chloride (0.43 mL, 5.0 mmol) in CH2Cl2 (20 mL) at -78° C. was added DMSO (0.52 ml, 7.0 mmol) dropwise. After gas evolution subsided (~5 minutes) the alcohol 11 (0.8 g, 3.5 mmol) in CH2Cl2 (20 mL) was added in a stream. After 20 minutes triethylamine (1.7 mL, 12 mmol) was added dropwise and then the cooling bath removed. After 20 minutes (carbethoxymethylene) triphenylphosphorane (1.4 g, 4.0 mmol) was added. After 2.0 hours the reaction mixture was diluted with petroleum ether and then washed sequentially with H2O, 5% KHSO4, and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 15% ethyl acetate/hexanes) gave the ester 12 (0.57 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05264420 |
| Source dataset | uspto-grants-1993_11 |
| ORD ID | ord-f893610a75244ef295100dedd97561f3 |
| Source note | uspto-grants-1993_11 |