Diisopropylamine → 4-(((4-bromophenyl)sulfonyl)methyl)tetrahydro-2H-pyran-4-ol

HRID 1597438Notes

Reaction equation

HRID 1597438 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].O1CCCCC1.[O:30]1[CH:35]=[CH:34][C:33](=[O:36])[CH:32]=[CH:31]1>C1COCC1>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([CH2:13][C:33]2([OH:36])[CH2:34][CH2:35][O:30][CH2:31][CH2:32]2)(=[O:16])=[O:15])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 770141-Bromo-4-(methylsulphonyl)benzeneHCID 86644052tetrahydropyran 4H-pyran-4-oneHCID 178418339Butyllithium

Product 1

HCID 217001474-(((4-bromophenyl)sulfonyl)methyl)tetrahydro-2H-pyran-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −10° C. solution of diisopropylamine (0.35 mL) in THF (5 mL) was treated with n-BuLi (1 mL, 2.5M solution in hexanes), stiired for 15 min then added via canula to a −78 C solution of 4-bromophenyl methyl sulfone (534 mg) in THF (5 mL). Stirred for 1 h, then treated with tetrahydropyran-4H-pyran-4-one (0.21 mL) and stirred for an additional 1 h. The reaction was quenched with aq. NH4Cl, diluted with water and extracted wth EtOAc (3×). The combined organics were washed with brine, dried (Na2SO4), filtered, concentrated and purified via silica gel chromatography eluting with 10% ethyl acetate/dichloromethane to give 640 mg of the title compound.

Workup

  1. stirringstirred for an additional 1 h
  2. customThe reaction was quenched with aq. NH4Cl
  3. additiondiluted with water
  4. extractionextracted wth EtOAc (3×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via silica gel chromatography
  10. washeluting with 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-42d3a8be9b54433a9ba8eb2a0adc7ee8
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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