Diisopropylamine → beta-Hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile

HRID 2232801Notes

Reaction equation

HRID 2232801 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:6].[CH:19]([N-:22]C(C)C)(C)[CH3:20].[Li+].C(NC(C)C)(C)C.C([Li])CCC>O1CCCC1.CCCCCC.C(#N)C>[OH:6][C:5]([C:4]1[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=1[O:2][CH3:1])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH2:20][C:19]#[N:22]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 5847282,2'-DimethoxybenzophenoneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 14547225beta-Hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

As in Example 97, a solution of 2,2'-dimethoxybenzophenone (24.2 g) and acetonitrile (6 mL) in tetrahydrofuran (120 mL) was added to a chilled (-70° C.) solution of lithium diisopropylamide prepared from diisopropylamine (16 mL) and 1.55M n-butyl lithium in hexane (74 mL) in dry tetrahydrofuran (120 mL). After the reaction was kept at -70° C. for 15 minutes, it was allowed to warm to room temperature and then was worked up in the usual manner to furnish 26.4 g of beta-hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile, mp 170°-180° C. A sample was recrystallized from methanol to give the analytical specimen, mp 181°-182° C.

Sources & evidence

ORD record
ord-994925b769ca48cf9fa26145ed410605
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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