Sodium Hydroxide → (2-Thiophen-2-yl-benzoxazol-6-yl)methanol

HRID 1619997Notes

Reaction equation

HRID 1619997 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]2[CH:14]=[C:13]([C:15](OC)=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1.C(=O)=O.CC(C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1.O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 18522661Acetone cardiceHCID 21226445Aluminium lithium hydrideHCID 67466917Methyl 2-thiophen-2-yl-benzoxazole-6-carboxylate

Product 1

HCID 67466243(2-Thiophen-2-yl-benzoxazol-6-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

6.1 g (23.53 mmol) methyl 2-thiophen-2-yl-benzoxazole-6-carboxylate are dissolved in 300 ml THF and cooled with dry ice/acetone, then 40 ml (40.00 mmol) of 1M lithium aluminium hydride dissolved in THF are slowly added dropwise. The mixture is stirred for 30 min at 0° C., then 4 ml of water dissolved in 20 ml THF are added dropwise, followed by 4 ml of 4N sodium hydroxide solution and another 4 ml of water. The resulting suspension is mixed with magnesium sulphate and filtered through kieselguhr, the filtrate is concentrated by rotary evaporation i. V. and the residue is purified on silica gel (eluant: cyclohexane/EA).

Workup

  1. additionare slowly added dropwise
  2. additionare added dropwise
  3. filtrationfiltered through kieselguhr
  4. concentrationthe filtrate is concentrated by rotary evaporation i
  5. customand the residue is purified on silica gel (eluant: cyclohexane/EA)

Sources & evidence

ORD record
ord-18278e2e8faf427e9266b6afd69d55b7
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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