Tetrahydrofuran → N-[2-t-Butyl-5-(2-cyclohexyl-1-hydroxyethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 1734864Notes

Reaction equation

HRID 1734864 reaction equation
O1CCCC1.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:28][C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH3:9])([CH3:8])[CH3:7].[CH:36]1([CH2:42][Mg]Br)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)C>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:17])[CH2:42][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[O:28][C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 19966116N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamideHCID 178419664HCID 178419664, compound

Product 1

HCID 19966142N-[2-t-Butyl-5-(2-cyclohexyl-1-hydroxyethyl)phenyl]-2-(9H-xanthen-9-yl)acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

8 ml of a tetrahydrofuran solution containing 100 mg (0.25 mmol) of N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 15) were cooled in an ice bath. 0.38 ml (0.38 mmol) of a 1M solution of cyclohexylmethylmagnesium bromide in diethyl ether was then added dropwise to the solution. The resulting mixture was stirred for 20 minutes at this temperature. It was then diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 20 g of silica gel. Elution with mixtures of methylene chloride and ethyl acetate ranging from 7:1 to 2:1 by volume afforded 95 mg (yield 76%) of the title compound as a foam-like substance.

Workup

  1. temperaturewere cooled in an ice bath
  2. washwashed with dilute aqueous hydrochloric acid
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washElution with mixtures of methylene chloride and ethyl acetate ranging from 7:1 to 2:1 by volume

Sources & evidence

ORD record
ord-b8be42c75ab84edd929100695eacb2de
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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