Chlorotrimethylsilane → Methyl 4-methoxy-2-(1-methylethoxy)-3-(trimethylsilyl)benzoate

HRID 34958Notes

Reaction equation

HRID 34958 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13][CH:14]([CH3:16])[CH3:15])[CH:4]=1.Cl[Si:18]([CH3:21])([CH3:20])[CH3:19].C([N-]C(C)C)(C)C.[Li+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:13][CH:14]([CH3:16])[CH3:15])[C:4]=1[Si:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 2724682Lithium diisopropylamideHCID 14276512Methyl 2-isopropoxy-4-methoxybenzoate

Product 1

HCID 14276513Methyl 4-methoxy-2-(1-methylethoxy)-3-(trimethylsilyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

More specifically, Scheme 3 shows compound of the formula 9 is prepared by adding a mixture methyl 4-methoxy-2-(l-methylethoxy)benzoate of the formula (10) and chlorotrimethylsilane to a -70° C. -78° C. tetrahydrofuran solution of lithium diisopropylamide to give methyl 4-methoxy-2-(1-methylethoxy)-3-(trimethylsilyl)benzoate (11) regioselectively.

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-40ec61ce8c2f496c85fcb741cdbab0f2
Source dataset
uspto-grants-1988_08
Patent number
US04764525

Reaction notes

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