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Sulfuric acid magnesium salt (1:1) → (R,E)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2-sulfinamide

HRID 1908672
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HRID 1908672 반응식
[CH3:1][C:2]([S@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O-]S([O-])(=O)=O.[Mg+2].[Si:31]([O:38][CH2:39][CH:40]=O)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C(Cl)Cl>[C:34]([Si:31]([CH3:33])([CH3:32])[O:38][CH2:39][CH:40]=[N:7][S@@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])([CH3:37])([CH3:36])[CH3:35]
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참가 물질

6

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

생성물 1

HCID 86644143(R,E)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2-sulfinamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(R)-(+)-2-methyl-2-propanesulfinamide (8.70 g, 71.8 mmol), pyridinium p-toluenesulfonate (0.902 g, 3.59 mmol) and MgSO4 (43.2 g, 359 mmol) was suspended in methylene chloride (25 mL). A solution of (tert-butyldimethylsilyloxy)acetaldehyde (25.0 g, 144 mmol) dissolved in methylene chloride (10 mL) was added drop wise at room temperature. The reaction was stirred at room temperature overnight. The mixture was evaporated to dryness. Flash chromatography (silica, EtOAc/heptanes 1:4) gave the title compound as an oil that slowly solidified upon standing (18.3 g, 92%) sufficiently pure for the next step.

후처리

  1. additionwas added drop wise at room temperature
  2. customThe mixture was evaporated to dryness

출처 및 근거

ORD 기록
ord-d8e356925a0a4596a9e37522b4528a05
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598213B2

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