Aluminium lithium hydride → HCID 69057883, compound

HRID 859631Notes

Reaction equation

HRID 859631 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH3:14])=[CH:9][C:8]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:16]([O:15][C:8]1[CH:9]=[C:10]([CH2:13][CH3:14])[CH:11]=[CH:12][C:7]=1[CH:6]=[CH:5][CH2:4][OH:3])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69054353HCID 69054353, compound

Product 1

HCID 69057883HCID 69057883, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 3-(2-benzyloxy-4-ethyl-phenyl)-acrylic acid ethyl ester (2.9 g, 9.3 mmol) dissolved in ether (7 mL) was added to a cooled 0° C. suspension of lithium aluminium hydride (0.89 g, 23.4 mmol) in ether (20 mL). The reaction mixture was stirred for 4 hours, quenched with H2O (3.6 mL) and 15% NaOH (0.9 mL) and then filtered through glass frit washing with ether. The filtrate was concentrated to a clear oil and purified by flash column chromatography (0% to 30% EtOAc in hexanes) to give the product (1.78 g, 71%). 1H NMR (400 MHz, CDCl3): δ 6 1.22 (t, J=7.6 Hz, 3 H), 2.62 (q, J=7.6 Hz, 2 H), 4.29 (m, 2 H), 5.10 (s, 2 H), 6.35 (dt, J=16.2, 7.6 Hz, 1 H), 6.78 (s, 1 H), 6.80 (d, J=7.1 Hz, 1 H), 6.95 (d, J=16.2 Hz, 1 H), 7.32–7.45 (m, 6 H).

Workup

  1. additionwas added to a cooled 0° C.
  2. customquenched with H2O (3.6 mL) and 15% NaOH (0.9 mL)
  3. filtrationfiltered through glass frit
  4. washwashing with ether
  5. concentrationThe filtrate was concentrated to a clear oil
  6. custompurified by flash column chromatography (0% to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-fbb740e34dfb499ba5e0c890412e32cb
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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