4-(Propane-1-sulfonyl)-benzaldehyde → HCID 67276042, compound

HRID 1698488Notes

Reaction equation

HRID 1698488 reaction equation
[CH2:1]([S:4]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>O1CCCC1>[CH:15]1([CH:11]([C:10]2[CH:13]=[CH:14][C:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[CH:8][CH:9]=2)[OH:12])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 204932624-(Propane-1-sulfonyl)-benzaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 67276042HCID 67276042, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 4-(propylsulphonyl)benzaldehyde (0.58 g) in dry tetrahydrofuran (5 mL), at −78° C. under nitrogen, was added a 0.5 M solution of cyclopropylmagnesium bromide in tetrahydrofuran (6.0 mL), slowly with stirring. The mixture was stirred for 1.75 h, quenched by addition of acetic acid (0.5 mL), then warmed to room temperature and partitioned between ethyl acetate and water. The organic phase was washed with brine, solvent stripped, and the residue chromatographed on silica gel, eluent 35% to 50% ethyl acetate in isohexane, to give the title compound as a white solid. 1H NMR (360 MHz, CDCl3) δ 7.88 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.4 Hz), 4.10 (1H, m), 3.06 (2K, m), 2.14 (1H, d, J=2.9 Hz), 1.75 (2H, m), 1.18 (1H, m), 0.99 (3H, t, J=7.4 Hz), 0.66 (2H, m), 0.49 (2H, m).

Workup

  1. stirringThe mixture was stirred for 1.75 h
  2. customquenched by addition of acetic acid (0.5 mL)
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine, solvent
  5. customthe residue chromatographed on silica gel, eluent 35% to 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-f7025c133fbb411f9b02b11fb7d637dc
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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