Water → HCID 20217094, compound

HRID 236336Notes

Reaction equation

HRID 236336 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([C:14]1[CH:15]=[C:16]([CH:20]([C:23]2[NH:24][CH:25]=[CH:26][CH:27]=2)CC)[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+].[CH3:31][CH2:32]OCC>>[O:7]([C:14]1[CH:19]=[C:18]([CH2:17][CH2:16][CH2:20][C:23]2[NH:24][CH:25]=[CH:26][CH:27]=2)[CH:31]=[CH:32][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 962Water2×HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131715059HCID 131715059, compound

Product 1

HCID 20217094HCID 20217094, compound

Procedure

To a slurry of lithium aluminum hydride 1.0892 g (27.3 mmol) in 200 ml of ether under a nitrogen atmosphere, a solution of 2 g (6.82 mmol) of 1-hydroxy-3-(3-phenoxyphenyl-1-(2-pyrrolyl)propane, dissolved in ether was added over a period of 5 min. The mixture was stirred at room temperature for 19 hours and then refluxed for an additional 75 min. The mixture was cooled in an ice bath and 1 ml of water was added followed by 1 ml of 15% w/w NaOH solution followed by 3 ml of water. The mixture was stirred for 30 min. The solids were filtered off and the filtrate was evaporated to dryness yielding 2 g of amber oil. After three chromatographic runs (on silica gel for dry column chromatography), in which the eluants were mixtures of ethyl acetate and hexane, 1.26 g of pure product 10 was obtained as an oil.

Workup

  1. additionwas added over a period of 5 min
  2. temperaturerefluxed for an additional 75 min
  3. temperatureThe mixture was cooled in an ice bath
  4. stirringThe mixture was stirred for 30 min
  5. filtrationThe solids were filtered off
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9f8291b96f8340e5a059b0c1e2e741c5
Source dataset
uspto-grants-1987_02
Patent number
US04644009

Reaction notes

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