Aluminium lithium hydride → HCID 86684710, compound

HRID 870489Notes

Reaction equation

HRID 870489 reaction equation
[C:1]([O:5][C@H:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7](OCC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[C:1]([O:5][C@H:6]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:7][OH:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86684709HCID 86684709, compound

Product 1

HCID 86684710HCID 86684710, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50-mL round-bottom flask was placed tetrahydrofuran (10 mL), 117.2 (500 mg, 2.12 mmol, 1.00 equiv) and LiAlH4 (81 mg, 2.13 mmol, 1.01 equiv). The resulting solution was stirred for 2 h at 0° C. in a water/ice bath. The reaction was then quenched by the addition of 20 mL of ethyl acetate. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). Purification afforded 0.38 g (92%) of (2R)-2-(tert-butoxy)-2-phenylethan-1-ol (117.3) as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask was placed
  2. customThe reaction was then quenched by the addition of 20 mL of ethyl acetate
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customPurification

Sources & evidence

ORD record
ord-430aa6c379a740f8a0846d49de0b96f5
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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