Tert-Butanesulfinamide → HCID 86635963, compound

HRID 1698515Notes

Reaction equation

HRID 1698515 reaction equation
[CH:1]1([CH2:4][S:5][C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:14]([S:18]([NH2:20])=[O:19])([CH3:17])([CH3:16])[CH3:15]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH:1]1([CH2:4][S:5][C:6]2[CH:13]=[CH:12][C:9](/[CH:10]=[CH:15]/[C:14]([CH3:17])([S:18]([NH2:20])=[O:19])[CH3:16])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 57959838HCID 57959838, compound

Product 1

HCID 86635963HCID 86635963, compound

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(cyclopropylmethyl)thio]benzaldehyde (5.64 g, 29.4 mmol) in THF (250 mL) was added tert-butyl sulphinamide (5.4 g, 44 mmol) and titanium(IV) ethoxide (12.6 mL, 60 mmol). The reaction mixture was stirred at room temperature for 3 d then quenched with water (250 mL) and ethyl acetate (250 mL). The mixture was stirred vigorously for 30 min then filtered through Celite, washing well with ethyl acetate. The organic phase was separated, dried (MgSO4) and concentrated to give the title compound as an oil. 1H NMR δ (360 MHz, CDCl3) δ 8.52 (1H, s), 7.74 (2H, d, J=8.3 Hz), 7.36 (2H, d, J=8.4 Hz), 2.95 (2H, d, J=7.0 Hz), 1.26 (9H, s), 1.14-1.06 (1H, m), 0.66-0.60 (2H, m), 0.34-0.29 (2H, m).

Workup

  1. customthen quenched with water (250 mL) and ethyl acetate (250 mL)
  2. stirringThe mixture was stirred vigorously for 30 min
  3. filtrationthen filtered through Celite
  4. washwashing well with ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d39ce38115d9464dbd179d73c93da496
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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