Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → Tert-butyl 3-methoxy-4-(1-methoxy-2-methyl-1-oxopropan-2-yl)benzoate

HRID 2204186Notes

Reaction equation

HRID 2204186 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16].[CH3:17][O:18][C:19]([O:23][Si](C)(C)C)=[C:20]([CH3:22])[CH3:21]>CN(C=O)C.[F-].[F-].[Zn+2]>[CH3:16][O:15][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:2]=1[C:20]([CH3:22])([CH3:21])[C:19]([O:18][CH3:17])=[O:23])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 25307097tert-Butyl 4-bromo-3-methoxybenzoate

Product 1

HCID 58550749Tert-butyl 3-methoxy-4-(1-methoxy-2-methyl-1-oxopropan-2-yl)benzoate

Reagents, catalysts & solvents 2

HCID 10129912Zinc(II) fluorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a microwave vial was added ZnF2 (36 mg, 0.35 mmol) and Pd(tBu3P)2 (7.2 mg, 0.014 mmol). The reaction vessel was purged with nitrogen for 10 minutes before tert-butyl 4-bromo-3-methoxy-benzoate (200 mg, 0.70 mmol) dissolved in DMF (2.5 mL) was added followed by (1-methoxy-2-methyl-prop-1-enoxy)-trimethyl-silane (180 mg, 1.1 mmol). The reaction vessel was placed in an 80° C. oil bath under an atmosphere of nitrogen and the mixture was allowed to stir overnight. The mixture was allowed to cool to rt and was filtered through a frit and was washed with brine and EtOAc. The organics were separated and dried over sodium sulfate. The solvent was removed and the residue was taken on to the next step without additional purification. ESI-MS m/z calc. 308.2, found 309.4 (M+1)+; Retention time: 3.12 minutes (4 min run).

Workup

  1. additionwas added
  2. customwas placed in an 80° C.
  3. filtrationwas filtered through a frit
  4. washwas washed with brine and EtOAc
  5. customThe organics were separated
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed
  8. customthe residue was taken on to the next step without additional purification
  9. customRetention time: 3.12 minutes (4 min run)

Sources & evidence

ORD record
ord-34dbda955b86410cb3f7ecff5208401e
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…