Aluminium lithium hydride → HCID 11514269, compound

HRID 2224688Notes

Reaction equation

HRID 2224688 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([NH:12][CH2:13][CH2:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]C(=O)C)=[CH:22][CH:21]=2)=[CH:17][CH:16]=1)=O)C>O1CCCC1>[CH3:10][NH:12][CH2:13][CH2:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59717846HCID 59717846, compound

Product 1

HCID 11514269HCID 11514269, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0M Lithium aluminum hydride in tetrahydrofuran (5 mL) was added to a solution of acetic acid 4-[4-(2-ethoxycarbonylamino-ethyl)-phenoxy]-phenyl ester (330 mg, 1.0 mmol) in tetrahydrofuran (25 mL). Refluxed overnight, cooled to room temperature, then quenched the reaction with saturated aqueous ammonium chloride and stirred for 3 hours. Decanted the organic layer. Washed the remaining solid with ethyl acetate (2×30 mL). Combined all the organic washes then concentrated on a rotary evaporator to yield 4-[4-(2-Methylamino-ethyl)-phenoxy]-phenol (200 mg): HPLC=98% (5/95 to 95/5 ACN/(0.1% TFA in water) over 10 minutes, Zorbax SB-Phenyl 4.6 mm×15 cm×5 micron, λ=254 nM. 1H NMR (CDCl3, 300.00 MHz): 7.42-6.77 (m, 8H), 4.32 (s, 1H), 2.95-2.79 (m, 4H), 2.52 (s, 3H). Step 2 4-{4-[2-(Benzyl-methyl-amino)-ethyl]-phenoxy}-phenol

Workup

  1. temperatureRefluxed overnight
  2. customquenched
  3. customthe reaction with saturated aqueous ammonium chloride
  4. customDecanted the organic layer
  5. washWashed the remaining solid with ethyl acetate (2×30 mL)
  6. concentrationthen concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-23a409052c8d46f785c93cd60e5b7108
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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