Triphenylphosphine → 5-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 493179ノート

反応式

HRID 493179 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=2[CH:6]=1)=[O:4].[CH:15]([N:18]1[CH2:23][CH2:22][CH:21](O)[CH2:20][CH2:19]1)([CH3:17])[CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([O:14][CH:21]3[CH2:22][CH2:23][N:18]([CH:15]([CH3:17])[CH3:16])[CH2:19][CH2:20]3)=[CH:13][C:7]=2[CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 5363146Diisopropyl azodicarboxylateHCID 13662999Methyl 5-hydroxybenzo[b]thiophene-2-carboxylate

生成物 1

HCID 687252665-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The above prepared 5-hydroxy-benzo[b]thiophene-2-carboxylic acid methyl ester (0.143 g, 0.687 mmol) was dissolved in 3.4 mL of THF and treated successively at 10° C. with 1-isopropyl-piperidin-4-ol (0.197 g, 2 eq.), triphenylphosphine (0.360 g, 2 eq.) and DIAD (0.267 mL, 2 eq.), and the mixture then kept at ambient temperature for another 2 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=5/95), delivered 0.222 g of the title compound as light yellow oil.

後処理

  1. additionPouring
  2. extractionice, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

出典と根拠

ORDレコード
ord-0e3bb16c37384e02ac45d446f93c3223
出典データセット
uspto-grants-2009_05
特許番号
US07534788B2

反応ノート

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