Tert-Butanesulfinamide → HCID 58424580, compound

HRID 1408804Notes

Reaction equation

HRID 1408804 reaction equation
[CH3:1][C:2]([S:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Br:8][C:9]1[CH:10]=[C:11]2[C:21](=[CH:22][CH:23]=1)[O:20][C:14]1([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:13][C:12]2=O>C1COCC1.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[Br:8][C:9]1[CH:10]=[C:11]2[C:21](=[CH:22][CH:23]=1)[O:20][C:14]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH2:13]/[C:12]/2=[N:7]\[S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 10541879HCID 10541879, compound

Product 1

HCID 58424580HCID 58424580, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The compound of 2-methylpropane-2-sulfinamide (29.54 g, 244.2 mmol) was added the solution of 6-bromospiro[chroman-2,1′-cyclohexan]-4-one (78.97 g, 268.6 mmol) in dry THF (900 mL), and then tetraisopropoxytitanium (193.1 g, 488.3 mmol) was added, The reaction mixture was reflux overnight. The mixture was removed in vacuo, and then quenched by brine, extracted with ethyl acetate. The ethyl acetate was dried over anhydrous Na2SO4, filtered, and evaporated to give (E)-N-(6-bromospiro[chroman-2,1′-cyclohexane]-4-ylidene)-2-methylpropane-2-sulfinamide (50 g, 40%). 1H NMR (CDCl3): 1.30 (s, 10H), 1.51 (m, 5H), 1.62 (m, 4H), 1.83 (d, 2H), 3.07 (d, 1H), 3.43 (d, 1H), 5.29 (s, 2H), 6.79 (d, 1H), 7.41 (dd, 1H), 7.96 (d, 1H).

Workup

  1. temperatureThe reaction mixture was reflux overnight
  2. customThe mixture was removed in vacuo
  3. customquenched by brine
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-419144646d16460dab155ebff533d9b0
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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