Water → HCID 89998981, compound

HRID 1051356Notes

Reaction equation

HRID 1051356 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[CH3:12][C:13]([S@@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14].O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])/[CH:5]=[N:18]/[S@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 676963-Fluoro-p-anisaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89998981HCID 89998981, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-fluoro-4-methoxybenzaldehyde (2.0 g, 13 mmol) in THF (40 mL) was added (S)-2-methylpropane-2-sulfinamide (2.84 g, 23.4 mmol) and Ti(OEt)4 (5.92 g, 26.0 mmol). The reaction mixture was heated at 65° C. for 12 h. After cooling to RT, the mixture was poured into water. The solid was filtered, and the filtrate was extracted with EtOAc (3×100 mL). The filtrate was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (1:4) to afford 3.0 g (90%) of (S,E)-N-(3-fluoro-4-methoxybenzylidene)-2-methylpropane-2-sulfinamide (66). LCMS (ESI) m/z: 258.1 [M+H]+.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationThe solid was filtered
  3. extractionthe filtrate was extracted with EtOAc (3×100 mL)
  4. dry with materialThe filtrate was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with EtOAc/petroleum ether (1:4)

Sources & evidence

ORD record
ord-7b9f43d2292840429fd9a8e6ae8a6473
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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