Diethyl Ether → HCID 10308260, compound

HRID 2115264Notes

Reaction equation

HRID 2115264 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.C([O:14][C:15]([C:17]1[S:18][CH:19]=[C:20]2[C:26]=1[C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[O:23][C:22]1[CH:31]=[CH:32][CH:33]=[CH:34][C:21]2=1)=O)C>O>[C:17]1([CH2:15][OH:14])[S:18][CH:19]=[C:20]2[C:26]=1[C:25]1[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=1[O:23][C:22]1[CH:31]=[CH:32][CH:33]=[CH:34][C:21]2=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether3×HCID 10171967HCID 10171967, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 10308260HCID 10308260, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of LiAlH4 in dry ether (10 mmoles in 15 ml of dry ether) an ether solution of the ester 5 (2 mmoles in 15 ml of dry ether) was added drop by drop. The reaction mixture was stirred at room temperature for 4 hours. After the complete quantity of the ester had been reacted (the course of the reaction was followed by thin layer chromatography), the excess of LiAlH4 was decomposed by the addition of diethyl ether and water. The obtained white precipitate was filtered off and after drying on anhydrous Na2SO4 the filtrate was evaporated under reduced pressure. The crude product was purified by chromatography on a column to give a pure product in the form of yellowish crystals.

Workup

  1. additionwas added drop by drop
  2. filtrationThe obtained white precipitate was filtered off
  3. dry with materialafter drying on anhydrous Na2SO4 the filtrate
  4. customwas evaporated under reduced pressure
  5. customThe crude product was purified by chromatography on a column
  6. customto give a pure product in the form of yellowish crystals

Sources & evidence

ORD record
ord-3e9cad2317f440eeb295a10a421afa0a
Source dataset
uspto-grants-2008_10
Patent number
US07435834B2

Reaction notes

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