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

HRID 15408

반응식

HRID 15408 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-791f4186fc2a410a8b3514d9786fd950
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732596B2

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