HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1911512Generated: November 1, 2026
Phenol → (R)-2,2-dimethyl-4-phenoxymethyl-oxazolidine-3-carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/1911512
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Di-tert-butyl azodicarboxylate | HCID 97268 | — |
| Reactant | (R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | HCID 11053464 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-2,2-dimethyl-4-phenoxymethyl-oxazolidine-3-carboxylic acid tert-butyl ester | HCID 16106960 | 63.2% |
Reaction Steps
To a stirred solution of tert-butyl (R)-4-(hydroxymethyl)-2,2-dimethyl-3-oxazolidinecarboxylate (400 mg; CAS 108149-63-9) in THF (20 ml) were added phenol (197 mg), triphenylphosphine (573 mg) and di-tert-butyl azodicarboxylate (488 mg). The resulting yellow solution was stirred at 70° C. for 18 h overnight, then concentrated in vacuo. The crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->70:30) to give (R)-2,2-dimethyl-4-phenoxymethyl-oxazolidine-3-carboxylic acid tert-butyl ester (336 mg, 63%) as a colourless viscous oil. MS (ISP): 308.3 ([M+H]+)).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08604061B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-cb267195a7484643912f635120f360e7 |
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| Source note | uspto-grants-2013_12 |
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