Tert-Butanesulfinamide → HCID 66654499, compound

HRID 2036226Notes

Reaction equation

HRID 2036226 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:6]=1[CH:7]=O)[CH:2]=[CH2:3].[CH3:14][C:15]([S:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.O.C(Cl)Cl.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:6]=1[CH:7]=[N:20][S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])[CH:2]=[CH2:3]

Participants

7

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 44703325-Chloro-2-[(prop-2-en-1-yl)oxy]benzaldehyde

Product 1

HCID 66654499HCID 66654499, compound

Reagents, catalysts & solvents 4

HCID 76524Titanium tetraethoxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-allyloxy-5-chloro-benzaldehyde (8.55 g, 43.48 mmol, 1.0 eq.) and 2-methyl-2-propanesulfinamide (6.86 g, 56.64 mmol, 1.3 eq.) in THF (200 mL), titanium (IV) ethoxide (52.3 mL, 49.84 mmol, 1.1 eq.) was added dropwise. The reaction mixture was stirred at r.t. for 18 hours. The reaction mixture was diluted with water (1000 mL) and DCM (300 mL).The reaction mixture was filtered. The layers were separated. The aq. phase was extracted with DCM (2×200 mL). The comb. org. phases were washed with water (1×250 mL), sat. aq. NaCl soln. (1×150 mL), dried over MgSO4, and concentrated in vacuo. The residue was used without further purification.

Workup

  1. additionwas added dropwise
  2. filtrationwas filtered
  3. customThe layers were separated
  4. extractionThe aq. phase was extracted with DCM (2×200 mL)
  5. washphases were washed with water (1×250 mL), sat. aq. NaCl soln
  6. dry with material(1×150 mL), dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was used without further purification

Sources & evidence

ORD record
ord-7eca5ee093f04e5198b073613289f8b2
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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