Pentane → HCID 86627014, 화합물

HRID 473384

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HRID 473384 반응식
[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]

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 86627014HCID 86627014, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9362f4e4f81c41a1b262d3a38a89967f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633315B2

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