Dimethyl Sulfoxide → HCID 131721777, compound

HRID 352308Notes

Reaction equation

HRID 352308 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.C(Cl)(Cl)Cl.C(=O)=O.[Si:18]([O:35][C:36]1[CH:53]=[CH:52][C:51]2[C@@H:50]3[C@H:41]([C@H:42]4[C@@:46]([CH2:48][CH:49]3[OH:54])([CH3:47])[CH:45]3[O:55][CH2:56][CH2:57][O:58][CH:44]3[CH2:43]4)[CH2:40][CH2:39][C:38]=2[CH:37]=1)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl>[Si:18]([O:35][C:36]1[CH:53]=[CH:52][C:51]2[C@@H:50]3[C@H:41]([C@H:42]4[C@@:46]([CH2:48][C:49]3=[O:54])([CH3:47])[CH:45]3[O:55][CH2:56][CH2:57][O:58][CH:44]3[CH2:43]4)[CH2:40][CH2:39][C:38]=2[CH:37]=1)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86583683HCID 86583683, compoundHCID 131721778HCID 131721778, compound

Product 1

HCID 131721777HCID 131721777, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1.5 mL (16.5 mmol) of oxalyl chloride in 15 mL of freshly distilled dichloromethane was added dropwise 2.35 mL (33.0 mmol) of dimethyl sulfoxide at −65° C. (chloroform/dry ice bath) under argon atmosphere. After 10 minutes, a solution of 6.2 gm (10.9 mmol) of 3-tert-butyldiphenylsilyloxy-17-ethylenedioxyestra-1,3,5(10)-11-ol 38 in 15 mL of dichloromethane was added dropwise, and the reaction mixture was stirred for 40 minutes at the same temperature. Then, a 12 mL (87.3 mmol) of triethylamine was added at −65° C., slowly allowed to attain room temperature, washed with saturated NH4Cl solution, water, brine, and dried (Na2SO4). Evaporation of the solvent furnished a gum, which was chromatographed (15% ethyl acetate/hexanes) to afford 5.18 g (84%) the product 39.

Workup

  1. customto attain room temperature
  2. washwashed with saturated NH4Cl solution, water, brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent
  5. customfurnished a gum, which
  6. customwas chromatographed (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b5b9b24366e94cf6aed98c7374d15a1f
Source dataset
uspto-grants-2004_06
Patent number
US06747018B2

Reaction notes

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