m-Chloroperbenzoic acid → HCID 11767461, compound

HRID 1779842Notes

Reaction equation

HRID 1779842 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][CH:10]1[S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:55])C=1>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[O:18][CH:10]1[S:11](=[O:55])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11296621HCID 11296621, compound

Product 1

HCID 11767461HCID 11767461, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a stirred cooled (-78° C.) solution of 3 (130 g, 0.2 mol) in dichloromethane (400 mL) is added dropwise over a period of 20 min a solution of mCPBA (74%, 58.31 g, 0.25 mol) in dichloromethane (300 mL). The mixture is stirred and allowed to warm up to -30° C. The mixture is then filtered. The filtrate is washed with saturated aqueous sodium bisulfite (2×300 mL), sodium bicarbonate (2×400 mL), brine (400 mL) and water (2×400 mL). The organic layer is dried (Na2SO4) and concentrated. Flash chromatography (CH2Cl2 :EtOAC=9:1) of the residue furnishes sulfoxide mixture 4 (127 g, 95%) as a white solid (mp 120°-122° C.). TLC Rf =0.3 (solvent--EtOH:CH2Cl2 =1:9). IR (KBr): 3060, 3030, 2910, 2867, 1495, 1450, 1360, 1210, 1136, 1092, 1049 cm-1. 1H NMR (CDCl3): 7.72-7.14 (m, 25H), 5.12-4.42 (m, 9H), 4.40-3.30 (m, 6H). Anal. Calc. for C40H40O6S: C, 74.04; H, 6.22; S, 4.93. Found: C, 74.10; H, 6.26; S, 4.99.

Workup

  1. filtrationThe mixture is then filtered
  2. washThe filtrate is washed with saturated aqueous sodium bisulfite (2×300 mL), sodium bicarbonate (2×400 mL), brine (400 mL) and water (2×400 mL)
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-806271da974345e293f4c83234231325
Source dataset
uspto-grants-1997_05
Patent number
US05627270

Reaction notes

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