Ethyl Acetate → N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

HRID 594381Notes

Reaction equation

HRID 594381 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=O.[CH3:16][C:17]([S:20]([NH2:22])=[O:21])([CH3:19])[CH3:18].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:14]=[N:22][S:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 220843Dibenzo(b,d)furan-2-carboxaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 86695630N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of commercially available dibenzo[b,d]furan-2-carbaldehyde (1.992 g; 10.20 mmol), titanium(IV) ethoxide Ti(OEt)4 (3.98 ml; 19.00 mmol), and 2-methylpropane-2-sulfinamide (1.150 g; 9.49 mmol) in anh. THF (18 ml) was stirred at rt, under nitrogen, for 4 h. AcOEt and brine were added, and the organic layer was further washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM) afforded N-(dibenzo[b,d]furan-2-ylmethylene)-2-methylpropane-2-sulfinamide as a pale yellow solid. LC-MS (conditions A): tR=0.96 min.; [M+H]+: 300.33 g/mol.

Workup

  1. washthe organic layer was further washed with brine
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by FC (DCM)

Sources & evidence

ORD record
ord-52acc40b5af041ff86e04ebb99c8d6e1
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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