Iodine → Benzo[b]thiophen-7-yl-p-tolylmethanol

HRID 15408

反応式

HRID 15408 の反応式
Br[C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Mg].II.[CH3:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH:19]([C:18]3[CH:21]=[CH:22][C:15]([CH3:14])=[CH:16][CH:17]=3)[OH:20])[C:7]1=2

参加物

7

反応物 5

HCID 807IodineHCID 77254-MethylbenzaldehydeHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 120455387-Bromobenzo[b]thiophene

生成物 1

HCID 68717781Benzo[b]thiophen-7-yl-p-tolylmethanol収率 57%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A Grignard reagent was prepared using 7-bromobenzo-[b]thiophene (1.0 g), magnesium (0.13 g), a catalytic amount of iodine and tetrahydrofuran (3 mL) according to the general method. To the Grignard reagent solution was added a solution of 4-methylbenzaldehyde (0.62 g) in tetrahydrofuran (5 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred at room temperature overnight and a saturated ammonium chloride aqueous solution was added to the mixture. The mixture was extracted with diethyl ether, and the organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). Further purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1) gave the title compound (0.68 g) as yellow oil.

後処理

  1. extractionThe mixture was extracted with diethyl ether
  2. washthe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  6. customFurther purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1)

出典と根拠

ORDレコード
ord-791f4186fc2a410a8b3514d9786fd950
出典データセット
uspto-grants-2010_06
特許番号
US07732596B2

関連ノート

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