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Acetic Acid → Ethyl 4,5,6,7-tetramethoxy-2-[4-(4-methoxycarbonylphenoxy)butyl]-1-oxo-2-indancarboxylate

HRID 2268464
ノート
印刷プレビュー

反応式

HRID 2268464 の反応式
C([Li])CCC.Br[C:7]1[C:12]([CH2:13][C:14]([C:35](OCC)=O)([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([O:40][CH3:41])[C:10]([O:42][CH3:43])=[C:9]([O:44][CH3:45])[C:8]=1[O:46][CH3:47].C(O)(=[O:50])C.C(=O)(O)[O-].[Na+]>C1COCC1.CCCCCC>[CH3:41][O:40][C:11]1[C:10]([O:42][CH3:43])=[C:9]([O:44][CH3:45])[C:8]([O:46][CH3:47])=[C:7]2[C:12]=1[CH2:13][C:14]([CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:35]2=[O:50]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 18348654Ethyl 2-(6-bromo-2,3,4,5-tetramethoxybenzyl)-2-ethoxycarbonyl-6-(4-methoxycarbonylphenoxy)hexanoateHCID 178418339Butyllithium

生成物 1

HCID 18348656Ethyl 4,5,6,7-tetramethoxy-2-[4-(4-methoxycarbonylphenoxy)butyl]-1-oxo-2-indancarboxylate収率 50.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A hexane solution of n-butyl lithium (1.68 M, 3.27 ml, 5.50 mmols) was dropwise added to a THF (30 ml) solution of ethyl 2-(6-bromo-2,3,4,5-tetramethoxybenzyl)-2-ethoxycarbonyl-6-(4-methoxycarbonylphenoxy)hexanoate (3.00 g, 4.58 mmols), under a nitrogen stream at −90° C. or lower, and stirring was continued for 15 minutes. Then, the temperature was raised to −78° C., and stirring was further continued for 15 minutes. To the reaction mixtures was added a THF (5 ml) solution of acetic acid (1.38 g, 22.9 mmols) at −70° C. or lower, which was then allowed to warm to room temperature, and a saturated aqueous sodium bicarbonate solution was added thereto, which was then extracted with diethyl ether. The organic layer waswashed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, and the resulting crude product was purified by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (1.22 g) as crystals.

後処理

  1. stirringstirring
  2. waitwas further continued for 15 minutes
  3. customTo the reaction mixtures
  4. temperatureto warm to room temperature
  5. extractionwhich was then extracted with diethyl ether
  6. dry with materiala saturated aqueous sodium chloride solution, and then dried
  7. customThe solvent was evaporated out
  8. customthe resulting crude product was purified by recrystallization (from hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-6651d75278e14a9b98ca46da7429ee17
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326369B1

反応ノート

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