Sodium Chloride → HCID 89755595, compound

HRID 714017Notes

Reaction equation

HRID 714017 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O)[CH3:2].[C:14]([S@:18]([NH2:20])=[O:19])([CH3:17])([CH3:16])[CH3:15].[Na+].[Cl-]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])/[CH:7]=[N:20]/[S:18]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:19])[CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89755595HCID 89755595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
66 °C

Procedure

In the first step, a reaction flask was charged with 3-ethoxy-4-methoxybenzaldehyde (2.0 g, 11 mmol), (R)-tert-butylsulfinamide (Ellman's auxiliary) (1.5 g, 12.2 mmol, 1.1 equiv) and THF (20 vol) then treated with Ti(OEt)4 (4.6 mL, 22 mmol, 2.0 equiv, ˜20% Ti). The reaction was heated for ˜6 h at 65-67° C. then cooled to 20-25° C. and added to 2% aqueous NaCl (20 vol). The slurry was filtered and the white precipitate (titanium salts) was washed with EtOAc. The organic portion was dried with MgSO4 and concentrated to afford (E)-N-(3-ethoxy-4-methoxybenzylidene)-2-methylpropane-2-sulfinamide (Compound E).

Workup

  1. temperaturethen cooled to 20-25° C.
  2. filtrationThe slurry was filtered
  3. washthe white precipitate (titanium salts) was washed with EtOAc
  4. dry with materialThe organic portion was dried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6274f01375b640c990d22a91b8be5dc4
Source dataset
uspto-grants-2015_11
Patent number
US09187417B2

Reaction notes

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