Dichloromethane → HCID 18798690, compound

HRID 356513Notes

Reaction equation

HRID 356513 reaction equation
[C:1]([C:5]1[C:6]([S:16][S:17][C:18]2[CH:23]=[C:22]([CH3:24])[C:21]([O:25][CH2:26][CH2:27][OH:28])=[CH:20][C:19]=2[C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:7][C:8]([CH3:15])=[C:9]([CH:14]=1)[O:10][CH2:11][CH2:12][OH:13])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.C(N(C(C)C)CC)(C)C.[CH3:45][O:46][CH2:47]Cl.C[CH2:50][O:51][C:52](C)=O>>[CH3:30][C:29]([C:19]1[CH:20]=[C:21]([O:25][CH2:26][CH2:27][O:28][CH2:45][O:46][CH3:47])[C:22]([CH3:24])=[CH:23][C:18]=1[S:17][S:16][C:6]1[CH:7]=[C:8]([CH3:15])[C:9]([O:10][CH2:11][CH2:12][O:13][CH2:50][O:51][CH3:52])=[CH:14][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:32])[CH3:31]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 7864Chloromethyl Methyl EtherHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 18798679HCID 18798679, compound

Product 1

HCID 18798690HCID 18798690, compound

Procedure

The title compound was prepared using 7.0 g (29 mmol) of 2-{5-tert-butyl-4-[2-tert-butyl-4-(2-hydroxy-ethoxy)-5-methyl-phenyldisulfanyl]-2-methyl-phenoxy}ethanol (prepared in Example MMM), 200 mL of CH2Cl2, 15.2 g (118 mmol) of diisopropylethylamine and 9.45 g (118 mmol) of chloromethyl methyl ether. The reagents were mixed at 0° C. and stirred at that temperature for 1 hour. The reaction mixture was warmed to room temperature and stirred for 15 hours, then diluted with EtOAc and quenched with 1N HCl. The organic layer was washed with sodium bicarbonate solution and brine and dried (MgSO4). The solvents were removed, and the residue was subjected to flash silica gel chromatography, eluting with EtOAc:hexane (5:95, then switching to 1:4).

Workup

  1. additionThe reagents were mixed at 0° C.
  2. stirringstirred for 15 hours
  3. customquenched with 1N HCl
  4. washThe organic layer was washed with sodium bicarbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. customThe solvents were removed
  7. washeluting with EtOAc:hexane (5:95

Sources & evidence

ORD record
ord-e35b83fa1dac4d00b16d9fecee718ca9
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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