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

HRID 605952ノート

反応式

HRID 605952 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].[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]

参加物

6

反応物 4

HCID 7766Diethyl CarbonateHCID 25517Ammonium ChlorideHCID 5462224Magnesium2 回HCID 120455387-Bromobenzo[b]thiophene

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-22bb57e40fff46cd9899190912f0b520
出典データセット
uspto-grants-2011_03
特許番号
US07915256B2

反応ノート

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