Diethyl Ether → HCID 76099180, compound

HRID 1682175Notes

Reaction equation

HRID 1682175 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])[CH2:9][CH2:10][CH3:11].[CH:13]([OH:16])([CH3:15])[CH3:14].CC[O:19]CC>O1CCCC1>[CH3:14][C:13]12[CH2:6][CH:5]([CH2:7][O:16]1)[CH:10]1[CH:9]([CH2:11]1)[C:15]2=[O:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 3776IsopropanolHCID 7912DiisopropylamineHCID 178418339Butyllithium

Product 1

HCID 76099180HCID 76099180, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To 2.38 ml (0.017 mol) diisopropylamine in 10 ml tetrahydrofuran at -78° C. was added dropwise 6.17 ml (0.015 mol) 2.5M butyllithium in hexanes. The reaction mixture was warmed in -20° C. and then cooled back to -78° C. To this solution was added dropwise 5.0 g (0.015 mol) 2-endo-(+/-)-5-methyl-2-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-6-oxabicyclo[3.2.1]-octan-4-one in 10 ml tetrahydrofuran. The reaction mixture was allowed to warm to ambient temperature and stirred for four hours. The reaction was cooled to 0° C. and 50 ml of isopropanol was added. Ether was added and organic layer was washed with water, dried over MgSO4, filtered, and concentrated to an oil. Flash chromatography in 20:1 hexanes:ethylacetate, followed by 6:1 hexanes:ethylacetate yielded 1.32 g of oil.

Workup

  1. temperaturecooled back to -78° C
  2. temperatureto warm to ambient temperature
  3. temperatureThe reaction was cooled to 0° C.
  4. washorganic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-345b22f86ba44a29945ccbe253fcb179
Source dataset
uspto-grants-1992_12
Patent number
US05175314

Reaction notes

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