Water → HCID 86724254, compound

HRID 594858Notes

Reaction equation

HRID 594858 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-25c02ac9257744f19fa6be8d4e92fa71
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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