Boron → 6,7-Dichloro-5-methoxy-2-n-propylbenzo[b]thiophene

HRID 1903507ノート

反応式

HRID 1903507 の反応式
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH:9](O)[CH:8]([CH2:11][CH2:12][CH3:13])[S:7][C:6]=2[C:14]=1[Cl:15].[B]>C(O)(=O)C>[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:11][CH2:12][CH3:13])[S:7][C:6]=2[C:14]=1[Cl:15]

参加物

4

反応物 2

HCID 5462311BoronHCID 13290182HCID 13290182、化合物

生成物 1

HCID 139528716,7-Dichloro-5-methoxy-2-n-propylbenzo[b]thiophene収率 75.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a mixture of 44 g of 6,7-dichloro-2,3-dihydro-3-hydroxy-5-methoxy-2-n-propylbenzo[b]thiophene in 275 ml of glacial acetic acid is added 65 ml of boron triluoride etherate and the mixture is warmed on a steam bath unitl it becomes clear. The solution is stired for 10 mins and then quenched with a mixture of 500 g of ice and 200 ml of a 10% sodium hydroxide solution. The mixture is neutralized with 50% sodium hydroxide solution and then extracted with two 300-ml portions of ethyl ether. The organic layers are combined, washed with 100 ml of a saturated sodium bicarbonate solution, 100 ml of water, dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give an oil. Chromatography of the oil on an alumina column using 9:1-hexane:ethyl ether as eluting solvent gives 31 g of 6,7-dichloro-5-methoxy-2-n-propylbenzo[b]thiophene as an oil.

後処理

  1. temperaturethe mixture is warmed on a steam bath unitl it
  2. customquenched with a mixture of 500 g of ice and 200 ml of a 10% sodium hydroxide solution
  3. extractionextracted with two 300-ml portions of ethyl ether
  4. washwashed with 100 ml of a saturated sodium bicarbonate solution, 100 ml of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent is removed
  8. customto give an oil
  9. wash1-hexane:ethyl ether as eluting solvent

出典と根拠

ORDレコード
ord-7d970c491a5649aebd560201e5cede08
出典データセット
uspto-grants-1984_03
特許番号
US04436748

反応ノート

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