Dibutyltin dichloride → 3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 749353

反応式

HRID 749353 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:17]1[O:27][C:20]2([CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]2)[O:19][CH2:18]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:23]1[CH2:24][CH2:25][C:20]2([O:27][CH2:17][CH2:18][O:19]2)[CH2:21][CH2:22]1)=[O:4]

参加物

6

反応物 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

生成物 1

HCID 597522913-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester収率 77.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (987 mg, 4.23 mmol) in dry THF (1.0 ml), at room temperature, was added 1,4-cyclohexanedione monoethylene ketal (661 mg, 4.23 mmol), followed by dibutyltin dichloride (129 mg, 0.42 mmol). After 5 min, phenyl silane (575 μL, 4.65 mmol) was added and the reaction mixture was stirred at room temperature for 4 days when a clear solution resulted. It was then concentrated and the residue purified by flash chromatography (0% to 30% EtOAc/Hexane) to obtain 1.22 g (77%) of 3-(1,4-Dioxa-spiro[4.5]dec-8-ylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester.

後処理

  1. customresulted
  2. concentrationIt was then concentrated
  3. customthe residue purified by flash chromatography (0% to 30% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-e03b4a58974245c6ad7b68dfb9adfeca
出典データセット
uspto-grants-2008_07
特許番号
US07402608B2

関連ノート

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