Diethyl Carbonate → Ethyl benzo[b]thiophene-7-carboxylate

HRID 605952노트

반응식

HRID 605952 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].[C:12](=O)([O:16]CC)[O:13][CH2:14][CH3:15].[Cl-].[NH4+]>C1COCC1>[CH2:14]([O:13][C:12]([C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:16])[CH3:15]

참가 물질

6

반응물 4

HCID 7766Diethyl CarbonateHCID 25517Ammonium ChlorideHCID 5462224Magnesium2회HCID 120455387-Bromobenzo[b]thiophene

생성물 1

HCID 49758023Ethyl benzo[b]thiophene-7-carboxylate수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

7-bromobenzo[b]thiophene (500 mg, 2.36 mmol) is dissolved in dry THF (5.0 mL) under nitrogen. Magnesium turnings (530 mg, 2.83 mmol, 1.20 equiv.) are added and the resulting mixture is heated at reflux until dissolution of the magnesium has occurred. The resulting cloudy yellow solution is allowed to cool to rt and diethyl carbonate (2 mL, excess) is added and stirring continued for one hour, when ammonium chloride (10% aq) is added. The resulting mixture is partitioned between DCM and water and the aqueous layer is extracted with DCM. The organic fractions are combined, washed with brine, dried over Na2SO4 and adsorbed onto silica. Purification by LC using 8/2 cyclohexane/dichloromethane as the eluent afforded the title compound as a pale orange oil (346.2 mg, 71%).

후처리

  1. temperaturethe resulting mixture is heated
  2. customThe resulting mixture is partitioned between DCM and water
  3. extractionthe aqueous layer is extracted with DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customPurification by LC

출처 및 근거

ORD 기록
ord-22bb57e40fff46cd9899190912f0b520
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915256B2

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