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Dimethylformamide → [4-Cyano-5-methyl-4-(2-formyl-5-thienyl)hexyloxy]-t-butyldimethyl Silane

HRID 1582771
ノート
印刷プレビュー

反応式

HRID 1582771 の反応式
[C:1]([C:3]([C:18]1[S:22][C:21](Br)=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])#[N:2].C([Li])CCC.CN(C)[CH:31]=[O:32].[Cl-].[NH4+]>O1CCCC1.CCCCCC.[Cl-].[Na+].O>[C:1]([C:3]([C:18]1[S:22][C:21]([CH:31]=[O:32])=[CH:20][CH:19]=1)([CH:15]([CH3:17])[CH3:16])[CH2:4][CH2:5][CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 22393724[4-Cyano-5-methyl-4-(2-bromo-5-thienyl)hexyloxy]-tert-butyldimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 22718248[4-Cyano-5-methyl-4-(2-formyl-5-thienyl)hexyloxy]-t-butyldimethyl Silane

試薬・触媒・溶媒 3

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒
HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of [4-cyano-5-methyl-4-(2-bromo-5-thienyl)hexyloxy]-t-butyldimethyl silane, 1.42 g 3.41 mmol, in tetrahydrofuran 20 ml was cooled to −70° C. A solution of 1.53 M butyl lithium in hexane 1.52 ml was added dropwise thereto and stirred for 10 minutes. N,N-dimethylformamide 1.52 ml was added thereto, and the temperature was raised to room temperature. Aqueous saturated ammonium chloride and brine were added to the reaction mixture which was then extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 515 mg 1.41 mmol, 41.3%, was obtained as a yellow syrup.

後処理

  1. extractionwas then extracted with ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 515 mg 1.41 mmol, 41.3%
  6. customwas obtained as a yellow syrup

出典と根拠

ORDレコード
ord-4b64be1cd62d4c03a10e539393a91cf0
出典データセット
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06737425B1

反応ノート

読み込み中…

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