Water → 7-Methyl-2,3-dihydro-1-benzofuran-3-ol

HRID 22927

反応式

HRID 22927 の反応式
[Cl-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[OH:9][C:10]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].O>C1COCC1>[CH3:18][C:17]1[C:10]2[O:9][CH2:2][CH:12]([OH:13])[C:11]=2[CH:14]=[CH:15][CH:16]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 5227773-Methylsalicylaldehyde

生成物 1

HCID 130130607-Methyl-2,3-dihydro-1-benzofuran-3-ol収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred suspension of trimethyl sulfoxonium chloride (3.78 g, 0.03 mole) in dry THF (60 ml) was added sodium hydride (1.16 g, 0.03 mole) and the whole warmed to reflux for 1 h. 2-Hydroxy-3-methyl-benzaldehyde (Lancaster) (4 g, 0.03 mole) was added in 30 ml THF via syringe and the resulting orange suspension stirred at reflux for 5 h. Water (50 ml) was added, and the organics were extracted with ether (3×50 ml). The combined organics were dried (MgSO4), filtered and evaporated in vacuo to an orange oil which was purified by column chromatography using 15-25% EtOAc in pentane to give the title product (2 g, 45%); 1HNMR (400 MHz, CDCl3) δ: 2.2 (s, 3H), 4.45 (m, 2H), 5.3 (m, 1H), 6.8 (t, 1H), 7.1 (d, 1H), 7.2 (d, 1H); LRMS: M+H, 151. (ES+).

後処理

  1. temperaturethe whole warmed
  2. temperatureto reflux for 1 h
  3. temperatureat reflux for 5 h
  4. extractionthe organics were extracted with ether (3×50 ml)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo to an orange oil which
  8. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-d002f44ed87c49ea9dd841d8b1506c3b
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

関連ノート

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