2,3-Diisopropoxy-4-methoxybenzaldehyde → 2,3-Diisopropoxy-1-(1-hydroxyethyl)-4-methoxybenzene

HRID 9309

Reaction equation

HRID 9309 reaction equation
[CH:1]([O:4][C:5]1[C:12]([O:13][CH:14]([CH3:16])[CH3:15])=[C:11]([O:17][CH3:18])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:3])[CH3:2].[CH3:19][Li]>C(OCC)C>[CH:1]([O:4][C:5]1[C:12]([O:13][CH:14]([CH3:16])[CH3:15])=[C:11]([O:17][CH3:18])[CH:10]=[CH:9][C:6]=1[CH:7]([OH:8])[CH3:19])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 219865542,3-Diisopropoxy-4-methoxybenzaldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 219865522,3-Diisopropoxy-1-(1-hydroxyethyl)-4-methoxybenzeneYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 22 (23.10 g, 91.56 mmol) in dry ethyl ether (150 mL) was added dropwise methyllithium (98.10 mL, 1.4 M in EtO2, 1.37.3 mmol) at 0° C. under nitrogen. The reaction mixture was stirred for 2 h allowing too reach room temperature. The reaction was slowly quenched with water, the phases were separated, and the aqueous phase was extracted with ethyl ether (3×150 mL). The combined organic solutions were dried over MgSO4 and concentrated over reduced pressure. Purification by flash column chromatography (silica gel, elution with hexanes/EtOAc: 80/20) provided the protected alcohol 20.62 g (76.77 mmol, 84%) as a pale yellow oil.

Workup

  1. customallowing too reach room temperature
  2. customThe reaction was slowly quenched with water
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl ether (3×150 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated over reduced pressure
  7. customPurification
  8. washby flash column chromatography (silica gel, elution with hexanes/EtOAc: 80/20)

Sources & evidence

ORD record
ord-984178fe26d140788905778d11aa6935
Source dataset
uspto-grants-2006_08
Patent number
US07091240B2

Linked notes

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