Water → Ethyl 4'-(3-isopropylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

HRID 253486ノート

反応式

HRID 253486 の反応式
[CH:1]([NH2:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:24][CH:23]=2)=[CH:18][C:17]=1[C:33]1[CH:42]=[CH:41][C:40]2[C:39]([CH3:44])([CH3:43])[CH2:38][CH2:37][C:36]([CH3:46])([CH3:45])[C:35]=2[CH:34]=1.O>C(#N)C>[CH:1]([NH:4][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:27]=2)=[CH:18][C:17]=1[C:33]1[CH:42]=[CH:41][C:40]2[C:39]([CH3:44])([CH3:43])[CH2:38][CH2:37][C:36]([CH3:46])([CH3:45])[C:35]=2[CH:34]=1)([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 66856963Ethyl 4'-(3-iodopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

生成物 1

HCID 11421168Ethyl 4'-(3-isopropylaminopropoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate収率 30.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

430 μl (5 mmol) of isopropylamine and 420 mg (3 mmol) of potassium carbonate are added to a solution of 600 mg (1 mmol) of ethyl 4′-(3-iodopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate in 50 ml of acetonitrile. The reaction mixture is stirred at reflux overnight. The reaction is stopped by adding water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on silica gel (50/50 heptane/ethyl acetate). 160 mg of ethyl 4′-(3-isopropylaminopropoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a yellowish solid (m.p.=171° C., yield=30%).

後処理

  1. temperatureat reflux overnight
  2. extractionis then extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe residue is then purified by chromatography on silica gel (50/50 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-80cee948fd0b462da4e4e62f084e01f9
出典データセット
uspto-grants-2011_01
特許番号
US07872026B2

反応ノート

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