m-Chloroperbenzoic acid → HCID 67865713, compound

HRID 1074130Notes

Reaction equation

HRID 1074130 reaction equation
[CH3:1][C@H:2]([CH:26]([CH3:28])[CH3:27])[CH2:3][C:4]1[CH:9]=[C:8]([S:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH2:19][C@H:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])[CH:13]=2)=[O:11])[CH:7]=[CH:6][C:5]=1[CH3:25].ClC1C=C(C=CC=1)C(OO)=[O:34]>ClCCl>[CH3:1][C@H:2]([CH:26]([CH3:28])[CH3:27])[CH2:3][C:4]1[CH:9]=[C:8]([S:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH2:19][C@H:20]([CH3:24])[CH:21]([CH3:22])[CH3:23])[CH:13]=2)(=[O:34])=[O:11])[CH:7]=[CH:6][C:5]=1[CH3:25]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67917128HCID 67917128, compound

Product 1

HCID 67865713HCID 67865713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-2,3-Dimethylbutyl-p-tolylsulfoxide (4) (52 mg, 0.2 mmol) was dissolved in 1.0 mL of anhydrous dichloromethane and 60 mg (0.3 mmol) of 3-chloroperoxybenzoic acid (80-85%, Sigma) added with stirring. The reaction mixture was stirred for 2 h and quenched with 10% sodium bicarbonate. More dichloromethane was added and the combined organic extracts were washed with aqueous sodium sulfite and brine and dried with MgSO4. The solvent was removed in vacuo and the crude sulfone was purified by silica gel flash chromatography using hexane ethyl acetate mixtures to afford sulfone (6) as a colorless oil. For analytical purposes this was also purified by HPLC (Zorbax Sil 9.4×25 cm column) using 10% ethyl acetate in hexane to give 42 mg of pure (2S)-sulfone (6): [α]D20 =+17 (c=3.5 in CHCl3); MS m/z (relative intensity) 240 (M+, 3), 197 (5), 157 (100), 92 (19), 91 (27), 85 (25), 84 (31), 43 (72); 1H NMR δ 0.77 (3H, d, J=7 Hz), 0.82 (3H, d, J=7.0 Hz), 1.00 (3H, d, J=7.0 Hz), 1.66-1.98 (2H, m), 2.45 (3H, s, CH3 -Aryl), 2.86 (1H, dd, J=8, 11 Hz), 3.06 (1H, dd, j=4, 12 Hz), 7.35 (2H, d, J=7.0 Hz, H-aryl ortho), 7.75 (2H, d, J=8, H-aryl ortho).

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. customquenched with 10% sodium bicarbonate
  3. additionMore dichloromethane was added
  4. washthe combined organic extracts were washed with aqueous sodium sulfite and brine
  5. dry with materialdried with MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe crude sulfone was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-4b17db7b5896407e86952b1bd1a70a3e
Source dataset
uspto-grants-1990_11
Patent number
US04973584

Reaction notes

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