tert-Butanol → HCID 69417195, compound

HRID 1766942Notes

Reaction equation

HRID 1766942 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:17](C=O)=[CH:16][O:15][CH:14]=1)([O:7][CH2:8][CH:9]=[CH2:10])([O:3][CH2:4][CH:5]=[CH2:6])=[O:2].CC(=CC)C.Cl([O-])=O.[Na+].[OH2:29].O.P([O-])(O)(O)=O.[Na+].[C:37]([OH:41])(C)(C)C>O>[CH2:8]([O:7][P:1]([O:11][CH2:12][C:13]1[CH:17]=[C:16]([C:37]([OH:41])=[O:29])[O:15][CH:14]=1)([O:3][CH2:4][CH:5]=[CH2:6])=[O:2])[CH:9]=[CH2:10]

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 46834798HCID 46834798, compound

Product 1

HCID 69417195HCID 69417195, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diallyl (4-formyl-3-furyl)methyl phosphate (97 mg, 0.34 mmol) obtained from Example 35-(4) and 2-methyl-2-butene (1.18 g, 19.9 mmol) were dissolved in tert-butyl alcohol (2.70 ml), and then a solution of sodium chlorite (122 mg, 1.35 mmol) and sodium dihydrogen phosphate dihydrate (1.034 g, 6.76 mmol) dissolved in water (1.2 ml) was added thereto with stirring in an ice bath. The mixture was stirred for 2 hours while warming spontaneously to room temperature, and partitioned between ethyl acetate and an aqueous solution of sodium chloride, then the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel (2 g) column (eluent; ethyl acetate) to afford the title compound (74 mg, 72% yield) as a colorless oil.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 2 hours
  3. custompartitioned between ethyl acetate
  4. dry with materialan aqueous solution of sodium chloride, then the organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-73b90a4859364186b94c32132d36ae13
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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