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delta-Gluconolactone → 1-Naphthalenemethanol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | delta-Gluconolactone | HCID 7027 | — |
| 反応物 | Boron trifluoride etherate | HCID 8000 | — |
| 反応物 | Triethylsilane | HCID 12052 | — |
| 反応物 | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| 生成物 | 1-Naphthalenemethanol | HCID 20908 | — |
反応手順
As in Reaction Scheme 2, lithium-halogen exchange of compound (76), followed by addition of the resulting nascent lithiated aromatic to perbenzylated gluconolactone (2), produces a mixture of the corresponding lactols, which is reduced using triethylsilane and boron trifluoride etherate. Subsequent desilylation using tetrabutylammonium fluoride (TBAF) affords 1-naphthalenemethanol (77) in a reasonable yield for the three steps.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08541380B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-bfedbb9e980745f9992a4ed0ae39d433 |
| 出典メモ | uspto-grants-2013_09 |