Diethyl Ether → HCID 54104552, compound

HRID 1637123Notes

Reaction equation

HRID 1637123 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[NH+:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[NH+]1C=C[CH:19]=[CH:18][CH:17]=1.[C:22]([O:25][C:26](=O)[CH3:27])(=O)[CH3:23].COC(=O)C[CH:33]([C:40]1[CH:45]=[CH:44][C:43](OC)=[C:42](OC2CCCC2)[CH:41]=1)[C:34]#[C:35][CH2:36][CH2:37][CH2:38]O.C[CH2:56][O:57][CH2:58]C>ClCCl>[CH:22]1([O:25][C:26]2[CH:27]=[C:36]([CH:35]([CH2:14][C:15]3[O:2][C:12]([CH3:13])=[CH:11][N:10]=3)[C:34]#[C:33][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:37]=[CH:38][C:56]=2[O:57][CH3:58])[CH2:19][CH2:18][CH2:17][CH2:23]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 2724130Cornforth reagentHCID 15463369HCID 15463369, compound

Product 1

HCID 54104552HCID 54104552, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of pyridinium dichromate (0.38 g, 1.0 mmol) and acetic anhydride (0.4 mL, 4.2 mmol) in dichloromethane (15 mL) was rapidly added a solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-4-[(N-propan-2-ol)-carboxamido]-1-phenylbut-1-yne (0.59 g, 1.4 mmol) in dichloromethane (5 mL) and the reaction was refluxed under an argon atmosphere for 7 h, then at room temperature for 3 d. The reaction was diluted with ether (30 mL), was filtered through Celite and was evaporated. Purification by flash chromatography, eluted with 1:1 ethyl acetate:hexanes provided the title compound (0.38 g, 64%) as a pale yellow solid, mp 105-106° C.

Workup

  1. temperaturethe reaction was refluxed under an argon atmosphere for 7 h
  2. filtrationwas filtered through Celite
  3. customwas evaporated
  4. customPurification by flash chromatography
  5. washeluted with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-c070899dddb84cb19048c1736175c586
Source dataset
uspto-grants-2000_03
Patent number
US06037367

Reaction notes

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