Water → HCID 86724254, compound

HRID 873712Notes

Reaction equation

HRID 873712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C:6]1([CH2:8][CH2:7]1)[C:5]2=O.[CH3:15][C:16]([S:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>C1COCC1.C([O-])C.C([O-])C.C([O-])C.C([O-])C.[Ti+4]>[Br:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C:6]1([CH2:8][CH2:7]1)[C:5]2=[N:21][S:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20]

Participants

6

Reactant 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 67236401HCID 67236401, compound

Product 1

HCID 86724254HCID 86724254, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 6-bromo-4H-spiro[chromene-3,1′-cyclopropan]-4-one (8.0 g, 32 mmol), 2-methylpropane-2-sulfinamide (12 g, 99 mmol), and titanium(IV) tetraethanolate (22 g, 95 mmol) in THF (160 ml) was stirred for 48 hours at 80° C. To the mixture was added H2O (20 ml), filtered through Celite and washed by EtOAc (50 ml). The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:EtOAc=100:0-0:100) to give N-(6-bromo-4H-spiro[chromene-3,1′-cyclopropan]-4-ylidene)-2-methylpropane-2-sulfinamide (6.5 g).

Workup

  1. filtrationfiltered through Celite
  2. washwashed by EtOAc (50 ml)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (hexane:EtOAc=100:0-0:100)

Sources & evidence

ORD record
ord-50115b91040c4edaafbfca896f33bb28
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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