Ethyl Acetate → HCID 67584017, compound

HRID 1456548Notes

Reaction equation

HRID 1456548 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:3]=1.CC(C)([O-])C.[K+].[C:24]([O:28][C:29]([N:31]1[CH2:35][C@H:34]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:33][C@H:32]1[CH2:44][CH2:45]Cl)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(OCC)(=O)C>CN(C)C(=O)C>[C:24]([O:28][C:29]([N:31]1[CH2:35][C@H:34]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:33][C@H:32]1[CH2:44][CH2:45][O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 22106952HCID 22106952, compoundHCID 23665647Potassium tert-butoxideHCID 57301849HCID 57301849, compound

Product 1

HCID 67584017HCID 67584017, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

248 mg of 4-fluoro-2-[2-(4-fluorophenyl)ethyl]phenol (prepared as described in Preparation 6) were dissolved in 10 ml of N,N-dimethylacetamide, and then 125 mg of potassium t-butoxide and 405 mg of (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(2-chloroethyl)pyrrolidine were added to the resulting solution, whilst ice-cooling. The resulting mixture was then stirred at room temperature for 3 hours, after which 150 ml of ethyl acetate were added to the reaction mixture. The reaction mixture was then washed with water and with a saturated aqueous solution of sodium chloride, in that order. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then concentrated by evaporation under reduced pressure. The resulting oily substance was purified by silica gel column chromatography, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 433 mg (yield 73%) of the title compound as a colorless oily substance.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was then washed with water and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe resulting oily substance was purified by silica gel column chromatography
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-5e3fb414f5f0486d988f206dfc925433
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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