Diisobutylaluminum hydride → (3,4-Dimethoxy-5-propylphenyl)methanol
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6]([O:15][CH3:16])[C:5]=1C.CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:16][O:15][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[C:7]=1[O:13][CH3:14])[CH2:3][OH:2]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of methyl 3,4-dimethoxy-5-propylbenzoic acid methyl ester (Example 1, Step 4, 6.0 g, 25.2 mmol) in DCM (400 mL) at −78° C. was added DIBAH (1.0 M in toluene, 76 mL, 76 mmol). The reaction mixture was stirred at −78° C. for 30 min then quenched with EtOAc (50 mL). The quenched reaction was warmed to room temperature then treated with 1:1 saturated aqueous potassium tartrate/saturated aqueous sodium bicarbonate (400 mL). The biphasic mixture was stirred vigorously for 30 min then the layers separated. The aqueous layer was extracted with EtOAc (300 mL), then the combined organic layer was dried over MgSO4, and concentrated to give 3,4-dimethoxy-5-propylbenzylalcohol (5.42 g, 100% yield). The product was used without further purification.
Workup
- customthen quenched with EtOAc (50 mL)
- customThe quenched reaction
- temperaturewas warmed to room temperature
- stirringThe biphasic mixture was stirred vigorously for 30 min
- customthe layers separated
- extractionThe aqueous layer was extracted with EtOAc (300 mL)
- dry with materialthe combined organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f112ff438b484893967950e6ccf665cb
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691843B2
Reaction notes
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