tert-Butanol → HCID 19812665, compound

HRID 1460401Notes

Reaction equation

HRID 1460401 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[C:13]=1COC.[CH3:26][Si](C[Li])(C)C.[C:32]([OH:36])(C)(C)C.C[C:38](C)([O-:40])C.[K+]>O1CCCC1.CCCCC.CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[C:13]=1[O:40][CH2:38][O:36][CH3:32])=[CH2:26]

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 19812690HCID 19812690, compoundHCID 23665647Potassium tert-butoxideHCID 178418939HCID 178418939, compound

Product 1

HCID 19812665HCID 19812665, compoundYield 277.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.84 g (5.1 mmol) of 2'-methoxymethoxy-3,4-dimethoxy-2-methoxymethylbenzophenone in 17 ml of dry tetrahydrofuran was cooled to 0° C. and 9.1 ml of 1.0M (9.1 mmol) of trimethylsilylmethyl lithium in pentane was added with stirring. After 2.5 hours, 0.38 ml (4.1 mmol) of t-butyl alcohol and 231 mg (2.0 mmol) of potassium t-butoxide were added and the mixture was heated at reflux with stirring for 4 hours. The resulting mixture was diluted with 40 ml of ether and the solution obtained was dried over magnesium sulfate and concentrated by evaporation under reduced pressure to obtain 2.0 g of an oil. This was purified by filtration chromatography on a 2 in. bed of silica gel eluting with hexane containing increasing amounts of ether to obtain the title compound as a clear oil. The proton and carbon NMR and infrared spectra were consistent with the assigned structure.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. stirringwith stirring for 4 hours
  4. customthe solution obtained
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-416b6bdff50b4064876544bac5549b23
Source dataset
uspto-grants-1991_12
Patent number
US05071465

Reaction notes

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