Diethyl Ether → HCID 86591570, compound

HRID 1294216Notes

Reaction equation

HRID 1294216 reaction equation
[CH3:1][CH:2]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:18]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)C.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCCCCC>[CH3:1][CH:2]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:18]=1)[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][OH:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 86591569HCID 86591569, compound

Product 1

HCID 86591570HCID 86591570, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of methyl 4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzoate (2.06 g) in tetrahydrofuran (30 mL) was dropwise added a solution (0.9 M, 30 mL) of diisobutylaluminum hydride in hexane at 0° C. and the mixture was stirred at room temperature for 2 hrs. Diethyl ether was added to the reaction mixture, sodium sulfate 10 hydrate was further added and the mixture was stirred for 2 hrs. After filtering off insoluble materials, the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give white crystals (1.85 g, 98%) of 4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzyl alcohol from a fraction eluted with ethyl acetate-hexane (1:1, v/v). melting point: 88-90° C.

Workup

  1. additionwas further added
  2. stirringthe mixture was stirred for 2 hrs
  3. filtrationAfter filtering off insoluble materials
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-793ae9b2979249fd84d1c90d69fbb7f1
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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