Sodium Hydroxide → HCID 57706049, compound

HRID 1662478Notes

Reaction equation

HRID 1662478 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16](O)=[O:17])=[CH:12][C:11]=1[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][C:11]=1[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57705619HCID 57705619, compound

Product 1

HCID 57706049HCID 57706049, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled solution of 67.20C (0.2929 g, 0.8893 mmol) in dry THF (10 mL) at 0° C. was added LAH (1M in THF) (1.8 mL, 1.8 mmol). Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 2 hours, 1N NaOH was added to quench the reaction (gas evolution occurred). The resulting solution was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to afford 67.20D as a colorless oil (231.8 mg, 83% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.25 (1H, d, J=9.0 Hz), 7.11 (4H, m), 6.82 (1H, dt, J=9.0, 3.5 Hz), 4.71 (2H, d, J=5.5 Hz), 3.81 (3H, s), 2.81 (4H, m), 1.69 (1H, s), 1.43 (6H, m).

Workup

  1. additionUpon complete addition
  2. customto quench
  3. customthe reaction (gas evolution occurred)
  4. extractionThe resulting solution was extracted three times with EtOAc
  5. dry with materialAfter drying over anhydrous magnesium sulfate, filtration, and concentration
  6. customthe residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes)
  7. additionFractions containing the desired product
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-014639e954e14709bed28a678b793370
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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