HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1976780Generated: October 31, 2026
Benzyl Alcohol → Benzyl 1-methyl-oxindole-5-carboxylate
https://huagongshe.com/reaction/1976780
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 5-Bromo-1-methyl-2-oxoindoline | HCID 2432666 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | Benzyl 1-methyl-oxindole-5-carboxylate | HCID 21998744 | — |
Reaction Steps
A solution of 5-bromo-1-methyl oxindole (3.75 g, 16.6 mmol) and triethylamine (3.48 mL) in THF (40 mL) was treated with benzyl alcohol (2.58 mL) and PdCl2(dppf) (300 mg), stirred under carbon monoxide (680 psi) at 130° C. for 16 hours, depressurized, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified on silica gel with 30% ethyl acetate/hexanes to provide 2.36 g of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06228868B1 |
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| Source dataset | uspto-grants-2001_05 |
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| ORD ID | ord-e1162bedb14248e2ae3d2451e161fd4e |
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| Source note | uspto-grants-2001_05 |
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