Water → HCID 118492030, compound

HRID 711338Notes

Reaction equation

HRID 711338 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].O>C(Cl)Cl>[CH3:13][C:14]([S@@:17]([N:19]=[CH:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:4]=1)=[O:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 679903-(Trifluoromethyl)benzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 118492030HCID 118492030, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(trifluoromethyl)benzaldehyde (5 g, 28.7 mmol) and (S)-2-methylpropane-2-sulfinamide (4.17 g, 34.4 mmol) in DCM (50 ml) at 0° C., was drop wise added Ti(O-iPr)4 (12 g, 43 mmol) under N2 atmosphere. After stirring for 20 h at room temperature, the reaction mixture was poured into water (100 mL) with vigorous stirring. The precipitate was filtered off and the filtrate was extracted with DCM (2×150 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1) to give the title compound (7 g, yield: 88%); m/z (ES+): 278 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered off
  2. extractionthe filtrate was extracted with DCM (2×150 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (PE/EtOAc=5/1 to 2/1)

Sources & evidence

ORD record
ord-d697bc10bbac49f7aed3f8dd1c853eda
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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