HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid → 4-{[Bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Cornforth reagent | HCID 2724130 | — |
| Reactant | Dibenzyl 4-hydroxy-2,2-dimethylbutyl phosphate | HCID 54009748 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-{[Bis(benzyloxy)phosphoryl]oxy}-3,3-dimethylbutanoic acid | HCID 54093655 | 85.1% |
Reaction Steps
To a solution of the product from Example 9B (0.396 g, 1.0 mmol) in DMF (10 mL) at room temperature was added pyridinium dichromate (2.3 g), and the mixture was stirred for 48 hours. 10% citric acid was added and the reaction was extracted twice with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient of 0-5% methanol in chloroform, to give the title compound (0.334 g, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426388B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-c49d69730f1c4e409055f192f5b34435 |
| Source note | uspto-grants-2013_04 |