Diethyl Ether → Rac.-3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrile
Reaction equation
C([O:4][C:5]1[C:6]([CH3:21])=[C:7]([CH3:20])[C:8]2[O:13][C:12]([CH3:17])([CH2:14][C:15]#[N:16])[CH2:11][CH2:10][C:9]=2[C:18]=1[CH3:19])(=O)C.C([O-])([O-])=O.[K+].[K+].CCOCC>CO.O>[OH:4][C:5]1[C:6]([CH3:21])=[C:7]([CH3:20])[C:8]2[O:13][C:12]([CH3:17])([CH2:14][C:15]#[N:16])[CH2:11][CH2:10][C:9]=2[C:18]=1[CH3:19]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 581 mg (2.02 mmoles) of rac.-6-acetyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrile and 418 mg (3.03 mmoles) of K2CO3 in 17 ml of methanol and 3 ml of water was stirred at room temperature for 64 hr. The resulting mixture was poured into water and worked-up with ether in the usual manner giving 480 mg of a tan solid. This material was triturated with cold ether to give 340 mg (69%) of a tan solid. A sample of this material was recrystallized from toluene yielding pure rac. 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrile as a tan solid mp 162°-163°.
Sources & evidence
- ORD record
- ord-fe0fc01730a848e2b3a107085a9874ad
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04186138
Reaction notes
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