Water → HCID 14627833, compound

HRID 1030237Notes

Reaction equation

HRID 1030237 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:16]=[C:15]([O:17][C:18]2[S:19][CH:20]=[C:21]([C:23](OCC)=[O:24])[N:22]=2)[CH:14]=[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=1[OH:32])([CH3:10])([CH3:9])[CH3:8].O.S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O1CCCC1>[C:28]([C:13]1[CH:14]=[C:15]([O:17][C:18]2[S:19][CH:20]=[C:21]([CH2:23][OH:24])[N:22]=2)[CH:16]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:12]=1[OH:32])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 14627818HCID 14627818, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14627833HCID 14627833, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.40 g) was suspended in 100 ml of diethyl ether, a solution (30 ml) of 0.80 g of 2,6-di-tert-butyl-4-[(4-ethoxycarbonyl-2-thiazolyl)oxy]phenol (produced in Example 40) in tetrahydrofuran was added to the suspension with stirring at room temperature, and the resultant mixture was stirred for further 4 hours. Water and then magnesium sulfate were added to the reaction mixture with cooling in an ice bath, and the resultant mixture was stirred for 15 minutes. The insoluble matter was filtered off, and the filtrate was concentrated. The crude product obtained was recrystallized from diethyl ether-hexane to give 0.30 g of the desired product as colorless crystals.

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationThe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe crude product obtained
  5. customwas recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-cb71341ca7944a50b6d407b96974876c
Source dataset
uspto-grants-1992_04
Patent number
US05104889

Reaction notes

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