Aluminium lithium hydride → HCID 43419458, compound

HRID 1675290Notes

Reaction equation

HRID 1675290 reaction equation
[C:1]([C:5]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:6]=1[O:7][CH2:8][C:9](OC)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([C:5]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:6]=1[O:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 28905805HCID 28905805, compound

Product 1

HCID 43419458HCID 43419458, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (methyl 2-(2-tert-butyl-5-methylphenoxy)acetate (7.16 g, 30.3 mmol) was added a 2.0M solution of LAH in THF (15.2 mL, 30.3 mL) under an ice-water bath. The resulting mixture was allowed to stir at room temperature for 10 minutes before it was quenched with ice chips. The solvent was removed, and 20 mL of 2.0N aqueous HCl solution was added. The resulting mixture was extracted with DCM (30 mL×3). The extract was washed with water, saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by CombiFlash to give 6.22 g of 46.3, which was eluted with 0-40% EtOAc in hexane.). MS ESI (pos.) m/e: 209 (+H). 1H NMR (400 MHz, CDCl3) δ 7.20 (d, J=8.0Hz, 1H), 6.76 (d, J=8.0Hz, 1H), 6.73 (s, 2H), 4.15 (dd, 2H), 4.04 (dd, 2H), 2.34 (s, 3H), 1.41 (s, 9H).

Workup

  1. customwas quenched with ice chips
  2. customThe solvent was removed
  3. addition20 mL of 2.0N aqueous HCl solution was added
  4. extractionThe resulting mixture was extracted with DCM (30 mL×3)
  5. washThe extract was washed with water, saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-942e954da2064480af1269cfd3f84f25
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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