Aluminium lithium hydride → 4-Hydroxymethyl-2-methoxyphenylboronic acid

HRID 2410104Notes

Reaction equation

HRID 2410104 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[C:6]([O:13][CH3:14])[CH:5]=1)(O)=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:11])[OH:12])=[C:6]([O:13][CH3:14])[CH:5]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 231342764-Borono-3-methoxybenzoic acid

Product 1

HCID 574973134-Hydroxymethyl-2-methoxyphenylboronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Carboxy-2-methoxyphenylboronic acid (500 mg, 2.5 mmol) was dissolved in THF (25 mL) and cooled to 0° C. At this temperature LAH (2 M solution in THF; 3.3 mL, 6.6 mmol) was added drop wise and the reaction mixture allowed to stir for 1 h at 0° C. and then allowed to warm to rt and stirred for 16 h. The reaction mixture was recooled to 0° C. and quenched by addition of MeOH. Celite and Na2SO4 were added, stirred for 15 min and then filtered. The filtrate was concentrated and the residue was dried under high vacuum to give the title compound which was used without further purification. tR: 0.46 min (LC-MS 2).

Workup

  1. temperatureto warm to rt
  2. stirringstirred for 16 h
  3. customwas recooled to 0° C.
  4. customquenched by addition of MeOH
  5. additionCelite and Na2SO4 were added
  6. stirringstirred for 15 min
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-7ff76d3763984b03bf669e6e4b9d6671
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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