Methyl chloroformate → 5-Methyl-4-triisopropylsilanyloxymethyl-furan-2-carboxylic acid methyl ester
Reaction equation
[CH:1]([Si:4]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[O:5][CH2:6][C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])([CH3:3])[CH3:2].C([Li])(CC)C.Cl[C:25]([O:27][CH3:28])=[O:26].[Cl-].[NH4+]>O1CCCC1>[CH3:28][O:27][C:25]([C:10]1[O:9][C:8]([CH3:12])=[C:7]([CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:13]([CH3:15])[CH3:14])[CH:16]([CH3:18])[CH3:17])[CH:11]=1)=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of triisopropyl-(2-methyl-furan-3-ylmethoxy)-silane (14) (10.0 g) in tetrahydrofuran (300 mL) was cooled to −78° C. with stirring was treated drop-wise with sec-butyllithium (3.0 M in cyclohexane, 37 mL). After 1 hour the reaction mixture was treated drop-wise with a solution of methyl chloroformate (5.2 g) in tetrahydrofuran (30 mL) over 10 mins and stirring was continued at −78° C. for 1 hour. The reaction mixture was then treated with saturated ammonium chloride solution (300 mL) and allowed to warm to ambient temperature. The two layers were separated and the organic phase washed with brine (300 mL), dried and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate/pentane (1:9 by volume) to give compound 15 as a clear oil.
Workup
- stirringstirring
- customThe two layers were separated
- washthe organic phase washed with brine (300 mL)
- customdried
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- washeluting with ethyl acetate/pentane (1:9 by volume)
Sources & evidence
- ORD record
- ord-7d3f5da89a88434d8c988b0287a11a5a
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196089B2
Reaction notes
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