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

HRID 1908672
Notes
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Reaction equation

HRID 1908672 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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)-(+)-

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-d8e356925a0a4596a9e37522b4528a05
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598213B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes