Hydrochloric Acid → HCID 11750834, compound

HRID 1791034Notes

Reaction equation

HRID 1791034 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]=[C:12]1[CH2:18][CH:17]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:16]2[CH:28]=[C:29]([C:32](=[O:34])[CH3:33])[CH:30]=[CH:31][C:15]=2[O:14][CH2:13]1.[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.Cl>O1CCCC1.ClCCl.O>[CH2:35]([C:17]1([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:16]2[CH:28]=[C:29]([C:32](=[O:34])[CH3:33])[CH:30]=[CH:31][C:15]=2[O:14][CH2:13][C:12](=[CH2:11])[CH2:18]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 11221558HCID 11221558, compound

Product 1

HCID 11750834HCID 11750834, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.152 ml (2.2 equivalents) of 1,3-dimethylpropyleneurea and then 1.286 ml (2.2 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 200 mg (0.58 mmol) of 1-[3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone, prepared according to example 13, in solution in 5.8 ml of tetrahydrofuran. The reaction medium then assumes a dark yellow color. After 15 minutes, 0.0698 ml (1 equivalent) of benzyl bromide is added. Water is immediately added, and 1N hydrochloric acid and dichloromethane. After separating the organic and aqueous phases, the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are washed with brine, are dried and are finally concentrated under vacuum. The crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 30/70) to provide 245 mg (97%) of 1-[5-benzyl-3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone in the form of a white solid; M.p.=131–132° C.

Workup

  1. customprepared
  2. customAfter separating the organic and aqueous phases
  3. extractionthe aqueous phase is extracted 3 times with dichloromethane
  4. washThe combined organic phases are washed with brine
  5. customare dried
  6. concentrationare finally concentrated under vacuum
  7. customThe crude reaction product
  8. customis purified by chromatography on silica gel (ethyl acetate/heptane 30/70)

Sources & evidence

ORD record
ord-e746e8ecaa2442ba976ac2c8f3d8b065
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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