関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Phenol | HCID 996 | — |
| 反応物 | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| 反応物 | p-Toluenesulfonate | HCID 85570 | — |
| 反応物 | (+/-)-3-[2-(Benzyloxy)-5-chloro-3-methoxyphenyl]-1,2-propanediol | HCID 68583190 | — |
| 反応物 | (+/-)-3-(5-Chloro-2-hydroxy-3-methoxyphenyl)-2-hydroxypropyl 4-methylbenzenesulfonate | HCID 86598563 | — |
| 反応物 | (+/-)-3-[2-(Benzyloxy)-5-chloro-3-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate | HCID 86598564 | — |
| 触媒 | Palladium | HCID 23938 | — |
| 溶媒 | Pyridine | HCID 1049 | — |
| 生成物 | (+/-)-(5-Chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate | HCID 86598566 | 76% |
反応手順
Treatment of (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]-1,2-propanediol (32 g, 0.1 mol) with p-toluenesulfonyl chloride (21 g, 0.11 mol) in pyridine generally according to the procedure described for intermediate 3 provided (±)-3-[2-(benzyloxy)-5-chloro-3-methoxyphenyl]-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the tosylate with palladium on carbon (2.32 g, 5 wt. %) generally according to the procedure described for Intermediate 4 afforded (±)-3-(5-chloro-2-hydroxy-3-methoxyphenyl)-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the phenol with triphenylphosphine (23.6 g, 0.09 mol) and diisopropyl azodicarboxylate (18.2 g, 0.09 mol) generally according to the procedure described for Intermediate 5 afforded 28 g (76%) of (±)-(5-chloro-7-methoxy-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as a pale yellow solid. mp 99-102° C.; Anal. calcd. for C17H17ClO5S: C, 55.36; H, 4.65. Found: C, 55.35; H, 4.62.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07435837B2 |
|---|
| 出典データセット | uspto-grants-2008_10 |
|---|
| ORD ID | ord-a1206852beab4ccaa29e1bd184f5c81f |
|---|
| 出典メモ | uspto-grants-2008_10 |
|---|
