Triethylamine → HCID 131721777, compound

HRID 651367Notes

Reaction equation

HRID 651367 reaction equation
C(Cl)(=O)C(Cl)=O.C(Cl)(Cl)Cl.C(=O)=O.[Si:14]([O:31][C:32]1[CH:49]=[CH:48][C:47]2[C@@H:46]3[C@H:37]([C@H:38]4[C@@:42]([CH2:44][CH:45]3[OH:50])([CH3:43])[CH:41]3[O:51][CH2:52][CH2:53][O:54][CH:40]3[CH2:39]4)[CH2:36][CH2:35][C:34]=2[CH:33]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[Si:14]([O:31][C:32]1[CH:49]=[CH:48][C:47]2[C@@H:46]3[C@H:37]([C@H:38]4[C@@:42]([CH2:44][C:45]3=[O:50])([CH3:43])[CH:41]3[O:51][CH2:52][CH2:53][O:54][CH:40]3[CH2:39]4)[CH2:36][CH2:35][C:34]=2[CH:33]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 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 sufoxide 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-28c8b2542e3b4809a39bc3cace6b7ca3
Source dataset
uspto-grants-2001_08
Patent number
US06281205B1

Reaction notes

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