Red-Al → HCID 69322475, compound
Reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH3:13][C:14]1([CH3:30])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH:28]=[O:29])[CH2:26][CH2:25][CH:24]=[CH:23][CH:22]1[CH3:27]>C1(C)C=CC=CC=1>[CH3:30][C:14]1([CH3:13])[CH:19]2[CH2:20][CH:16]([CH2:17][CH2:18]2)[CH:15]1[C:21]1([CH2:28][OH:29])[CH2:26][CH2:25][CH:24]=[CH:23][CH:22]1[CH3:27]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A 1-L reaction flask equipped with a stirrer, a thermometer, a reflux condenser, a heating mantle, and an addition funnel was charged with Vitride (300 g, 1.32 mol) and toluene (300 g). The resulting mixture was stirred at 20° C. The Diels-Alder product containing 1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2-methyl-cyclohex-3-enecarbaldehyde (300 g, 0.97 mol, synthesized as above in EXAMPLE VIII) was added over about 2 hours. The temperature was allowed to rise to 43° C. The reaction mass was aged for 3 hours. The excessive Vitride reagent was quenched with ethyl acetate (100 g), followed by sodium hydroxide (25%, 800 g). The temperature was allowed to rise to 50° C. and stirred for another 0.5 hours. The organic phase was washed with hot water (1 L) twice and concentrated to yield the crude product [1-(3,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-2-methyl-cyclohex-3-enyl]-methanol (295 g).
Workup
- customequipped with a stirrer
- additionwas added over about 2 hours
- customto rise to 43° C
- customThe excessive Vitride reagent was quenched with ethyl acetate (100 g)
- customto rise to 50° C.
- stirringstirred for another 0.5 hours
- washThe organic phase was washed with hot water (1 L) twice
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-427a246282534b2fbf71375a22876953
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183200B1
Reaction notes
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