Ammonium Chloride → HCID 12764994, 화합물

HRID 577441노트

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HRID 577441 반응식
[C:1]([Si:5]([CH3:11])([CH3:10])[O:6][CH2:7][C:8]#[CH:9])([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[Li+].[Cl-].CON(C)[C:22](=[O:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[Si:5]([O:6][CH2:7][C:8]#[C:9][C:22](=[O:24])[CH3:23])([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:10])[CH3:11]

참가 물질

7

반응물 5

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 3445622tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silaneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 12764994HCID 12764994, 화합물수율 70.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-10 °C

실험 절차

To a −40° C. solution of tert-butyl(dimethyl)(prop-2-yn-1-yloxy)silane (1.70 g, 10 mmol) in THF (6 mL) was added iPrMgCl.LiCl (8.46 mL, 11 mmol) dropwise keeping the internal temperature below −20° C. A solution of the N-methoxy-N-methylacetamide (1.13 g, 11.0 mmol) in THF (4 mL) was cooled to −10° C. and the alkyne solution was added to the Weinreb amide solution via cannula. The reaction mixture was stirred at −10° C. for 10 minutes. The reaction mixture was poured into a mixture of saturated NH4Cl and ice. The aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried with Mg2SO4, filtered, then concentrated under vacuum to give 5-{[tert-butyl(dimethyl)silyl]oxy}pent-3-yn-2-one (Cpd G, 1.5 g, 64%) as an oil.

후처리

  1. customthe internal temperature below −20° C
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-a0c48b8475a24d03a30a765b372359c5
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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