4-Methoxy-3-methylbenzyl chloride → HCID 22117274, compound

HRID 1275903

Reaction equation

C([Li])CCC.[CH3:6][C:7]1([CH3:20])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH3:19])=[N:8]1.Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[CH:24]=1>C1COCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:19][C:13]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=2[C:9]2[O:10][CH2:11][C:7]([CH3:20])([CH3:6])[N:8]=2)=[CH:24][C:25]=1[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

n-Butyllithium (14.4 ml, 2.5M solution in hexane) was added dropwise to a stirred solution of the product from step (i) (6.9 g) in THF (100 ml) at 0° C. The solution was stirred at 0° C. for 1 hour and then transferred by cannula into a solution of 4-chloromethyl-1-methoxy-2-methylbenzene (J. Chem. Soc. 1956, 2455) (5.86 g) in THF (60 ml) at -30° C. The mixture was stirred for 1 hour and allowed to warm to room temperature. After 30 minutes the reaction was quenched with water. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4) and evaporated. Purification was by chromatography eluting with 5% ethyl acetate in isohexane. Yield 2.16 g.

Workup

stirringThe mixture was stirred for 1 hour
temperatureto warm to room temperature
customAfter 30 minutes the reaction was quenched with water
customThe mixture was partitioned between ethyl acetate and water
washThe organic phase was washed with water
dry with materialdried (MgSO4)
customevaporated
customPurification
washeluting with 5% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-3586f2b78c074b26a38a61144b804e66
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06162808

Linked notes

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