Diethyl Ether → HCID 14051181, compound

HRID 1199708Notes

Reaction equation

HRID 1199708 reaction equation
C(OCC)C.C([O:8][C:9]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][CH:31]=1)/[CH:18]=[CH:19]/[C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:8][CH2:9][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][CH:31]=1)/[CH:18]=[CH:19]/[C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 14051732HCID 14051732, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14051181HCID 14051181, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 40 ml of ethyl ether was added 1.0 g of 2-[trans-3-(3-ethoxycarbonylpropoxy)styryl]benzothiazole, and 114 mg of lithium aluminum hydride was added under ice-cooling. After the mixture was stirred at the same temperature for 30 minutes, then at room temperature for 40 minutes, 114 μl of water, 114 μl of 15% aqueous sodium hydroxide and 340 μl of water were successively added slowly to decompose the aluminum complex, followed by extraction with toluene. After drying over anhydrous magnesium sklfate, the solvent was evaporated under reduced pressure and the crude crystals formed were washed with ethyl ether under ice-cooling, followed by drying under reduced pressure to give 570 mg (yield 64%) of the title compound.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. waitat room temperature for 40 minutes
  4. extractionfollowed by extraction with toluene
  5. dry with materialAfter drying over anhydrous magnesium sklfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe crude crystals formed
  8. washwere washed with ethyl ether under ice-
  9. temperaturecooling
  10. customby drying under reduced pressure

Sources & evidence

ORD record
ord-7f5865312c2345d596a5c9ffd84906cd
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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