Propylene Oxide → HCID 21996066, compound

HRID 1978031Notes

Reaction equation

HRID 1978031 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([Li])CCC.[CH2:23]1[O:26][CH:24]1[CH3:25]>C1COCC1>[O:11]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH2:1][CH2:23][CH:24]([OH:26])[CH3:25])(=[O:3])=[O:4])=[CH:10][CH:9]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 130785151-(Methanesulfonyl)-4-phenoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 21996066HCID 21996066, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-phenoxyphenyl methyl sulfone (1.0 g, 4.0 mmol) in 40 mL of THF at −78° C. was treated with n-butyllithium (1.6 mL, 2.5 M in hexanes), stirred 15 minutes at −78° C., treated with propylene oxide (257 μL), stirred from −78° C. to 23° C. over 16 hours, quenched with H2O, extracted with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated. Purification on silica gel with 1:1 hexanes/ethyl acetate provided 1.1 g (100%) of the desired product.

Workup

  1. stirringstirred from −78° C. to 23° C. over 16 hours
  2. customquenched with H2O
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification on silica gel with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-61559244b0114a0680967d217af5a7cf
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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