Pentane → HCID 86627014、化合物

HRID 473384

反応式

HRID 473384 の反応式
[CH3:1][Si:2]([CH3:7])([CH3:6])[C:3]#[C:4][CH3:5].CN(C)C(N(C)C)C.C([Li])(C)(C)C.CCCCC.[Si:26]([O:33][C@H:34]([CH2:43][O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])/[CH:35]=[N:36]/[S@:37]([C:39]([CH3:42])([CH3:41])[CH3:40])=[O:38])([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(OCC)C.C1COCC1>[Si:45]([O:44][CH2:43][C@@H:34]([O:33][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:28])[C@@H:35]([NH:36][S@:37]([C:39]([CH3:40])([CH3:41])[CH3:42])=[O:38])[CH2:5][C:4]#[C:3][Si:2]([CH3:7])([CH3:6])[CH3:1])([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46]

参加物

8

反応物 5

HCID 8003PentaneHCID 803631-(Trimethylsilyl)prop-1-yneHCID 17803068N~1~,N~1~,N'~1~,N'~1~-Tetramethylethane-1,1-diamineHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamideHCID 178418306HCID 178418306、化合物

生成物 1

HCID 86627014HCID 86627014、化合物

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Trimethyl(prop-1-ynyl)silane (4 mL, 28 mmol) and N,N,N′,N′-tetramethylethanediamine (5 mL, 36 mmol) were dissolved in dry diethyl ether (50 mL) and cooled to −78° C. Tert-butyllithium, 1.7 M solution in pentane (17 mL, 28 mmol) was added dropwise and the heterogenous solution was allowed to warm to 0° C. for 15 min to give a clear yellow solution, which was recooled to −78 C. Azeotropically (S,E)-N—((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (3.0 g, 7 mmol) in dry THF (20 mL) was added dropwise and the solution was stirred for 1 h until the starting material was consumed. The reaction mixture as quenched with NH4Cl and extracted with EtOAc. The combined organics were washed with water, brine, dried over Na2SO4, filtered, and concentrated to afford a yellow oil as (S)—N-((2S,3S)-1,2-bis(tert-butyldimethylsilyloxy)-6-(trimethylsilyl)hex-5-yn-3-yl)-2-methylpropane-2-sulfinamide.

後処理

  1. temperatureto warm to 0° C. for 15 min
  2. customto give a clear yellow solution, which
  3. customwas consumed
  4. customThe reaction mixture as quenched with NH4Cl
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-9362f4e4f81c41a1b262d3a38a89967f
出典データセット
uspto-grants-2014_01
特許番号
US08633315B2

関連ノート

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