Water → HCID 131718630, compound

HRID 1741586Notes

Reaction equation

HRID 1741586 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH:8]1[CH2:13][CH:12]([C:14](OCC)=[O:15])[S:11][C:10]2[S:19][CH:20]=[CH:21][C:9]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.CCOCC>[OH:15][CH2:14][CH:12]1[S:11][C:10]2[S:19][CH:20]=[CH:21][C:9]=2[CH:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:13]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131718631HCID 131718631, compound

Product 1

HCID 131718630HCID 131718630, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Compound 6 (23.5 g, 0.07 tool) was dissolved in tetrahydrofuran (50 ml). The solution was added dropwise under nitrogen to a stirred suspension of lithium aluminum hydride (3.3 g, 0.0875 mol) in anhydrous ether (100 ml) with cooling in ice. The mixture was stirred at ambient temperature for 15 hrs. The reaction was then cooled in ice and decomposed by carefully adding dropwise water (3.5 ml), 20% sodium hydroxide (2.6 ml) and water (12.3 ml). The mixture was diluted with ether (100 ml) and filtered. The solids were washed with ether. The combined ether solutions were washed with saturated sodium chloride, dried, filtered and concentrated in vacuo to yield 20.3 g 7 (50%) as a pale yellow oil.

Workup

  1. temperaturewith cooling in ice
  2. temperatureThe reaction was then cooled in ice
  3. filtrationfiltered
  4. washThe solids were washed with ether
  5. washThe combined ether solutions were washed with saturated sodium chloride
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cd5b0a7e9494ed088c12effcba44bee
Source dataset
uspto-grants-1994_08
Patent number
US05334591

Reaction notes

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