Tetrahydrofuran → HCID 140626495, compound

HRID 2279509Notes

Reaction equation

HRID 2279509 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])[CH:5]=O.[CH3:15][C:16]([S@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].C1COCC1>C(O[Ti](OCC)(OCC)OCC)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])/[CH:5]=[N:21]/[S@@:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 27788913-Chloro-4-(trifluoromethoxy)benzaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 140626495HCID 140626495, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-chloro-4-(trifluoromethoxy)benzaldehyde (2.8 g, 12 mmol) and (R)-2-methylpropane-2-sulfinamide (2.7 g, 22 mmol) and THF (25 mL) at RT was added tetraethoxytitanium (9.3 mL, 45 mmol) and the reaction was heated to 65° C. for 12 h. The reaction was cooled to RT, water (100 mL) was added and the solids were filtered and discarded. The filtrate was extracted with EtOAc, the organic fraction was dried, filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:10) to afford 3.8 g (98%) of (R,E)-N-(3-chloro-4-(trifluoromethoxy)benzylidene)-2-methylpropane-2-sulfinamide (218).

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationthe solids were filtered
  3. extractionThe filtrate was extracted with EtOAc
  4. customthe organic fraction was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with DCM/MeOH (500:10)

Sources & evidence

ORD record
ord-8aabd358c60f4d14bf0aa59db57629b2
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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