Lithium borohydride → HCID 58550743, compound

HRID 1478461Notes

Reaction equation

HRID 1478461 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[Li+].[BH4-]>O1CCCC1>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:14]([CH3:16])[CH3:15])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 18922523Methyl 3-formyl-4-isopropoxybenzoate

Product 1

HCID 58550743HCID 58550743, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-formyl-4-isopropoxy-benzoate (180 mg, 0.81 mmol) was dissolved in tetrahydrofuran (4.8 mL) and LiBH4 (35 mg, 1.6 mmol) was added. The reaction was stirred at room temperature for 30 minutes before it was quenched with methanol (3 mL). The reaction was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate (3 mL) and was then extracted with ethyl acetate (3×10 mL). The combined organics were washed with a saturated aqueous solution of sodium chloride (1×10 mL), dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure to yield methyl 3-(hydroxymethyl)-4-isopropoxy-benzoate (99%) as a viscous liquid. ESI-MS m/z calc. 224.3, found 225.3 (M+1)+; Retention time: 1.26 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 8.09 (s, 1H), 7.89 (d, J=8.6 Hz, 1H), 7.13 (d, J=8.6 Hz, 1H), 5.25 (t, J=5.6 Hz, 1H), 4.86-4.68 (m, 1H), 4.54 (d, J=5.6 Hz, 2H), 3.87 (s, 3H), 1.35 (d, J=6.0 Hz, 6H).

Workup

  1. customwas quenched with methanol (3 mL)
  2. additionThe reaction was neutralized by the addition of a saturated aqueous solution of sodium bicarbonate (3 mL)
  3. extractionwas then extracted with ethyl acetate (3×10 mL)
  4. washThe combined organics were washed with a saturated aqueous solution of sodium chloride (1×10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8f95f94fd08f4ecaab5d2b9602654400
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

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