Water → HCID 68815305, compound

HRID 733296Notes

Reaction equation

HRID 733296 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](=[O:25])[CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:11][C:10]=1[O:26][CH3:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:28]C(C)([O-])C.[K+].CI.O>C1COCC1.C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17](=[O:25])[CH:18]([CH3:28])[C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])=[CH:11][C:10]=1[O:26][CH3:27])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 68816019HCID 68816019, compound

Product 1

HCID 68815305HCID 68815305, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of (E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-6,6-dimethylhept-1-ene-3,5-dione (700 mg, 1.79 mmol) in THF (15 ml) under N2 was added potassium tert-butoxide (442 mg, 3.94 mmol) and stirred for a further 45 min at room temperature. A solution of methyl iodide (0.235 ml, 3.76 mmol) in THF (2 ml) was added and the mixture heated at reflux for 5 h. Water (25 ml) was added to the cooled mixture followed by DCM (25 ml). The organic layer was separated, washed with water (25 ml), dried (MgSO4(anh)), filtered and concentrated. The residue was purified by column chromatography on silica using dichloromethane as eluent to give the monomethyl alkylated product, (E)-1-(4-tert-butyldimethylsilyloxy-3-methoxyphenyl)-4,6,6-trimethylhept-1-ene-3,5-dione (540 mg, 74%):

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 h
  3. customThe organic layer was separated
  4. washwashed with water (25 ml)
  5. dry with materialdried (MgSO4(anh))
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-6e87602fec24468fa012f69f546faad3
Source dataset
uspto-grants-2009_09
Patent number
US07589123B2

Reaction notes

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