Tetrahydrofuran → HCID 59571047, compound

HRID 2192928Notes

Reaction equation

HRID 2192928 reaction equation
[BH4-].[Li+].C1COCC1.[CH3:8][O:9][C:10]1[CH:24]=[CH:23][C:13]([CH2:14][O:15][C:16]([CH3:22])([CH3:21])[C:17](OC)=[O:18])=[CH:12][CH:11]=1>O>[CH3:8][O:9][C:10]1[CH:24]=[CH:23][C:13]([CH2:14][O:15][C:16]([CH3:22])([CH3:21])[CH2:17][OH:18])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 59570909HCID 59570909, compound

Product 1

HCID 59571047HCID 59571047, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of lithium borohydride (2.29 g) and THF (200 mL) was added dropwise methyl 2-[(4-methoxybenzyl)oxy]-2-methylpropanoate (12.5 g) under ice-cooling, followed by stirring at 60° C. for 2 hours. To the reaction mixture was added water under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80) to obtain 2-[(4-methoxybenzyl)oxy]-2-methylpropan-1-ol (6.72 g) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80)

Sources & evidence

ORD record
ord-f8a4230430cb48a0aaa89f365a3baea1
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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