Oxiranemethanol, 4-methylbenzenesulfonate, (S)- → Toluene-4-sulfonic acid 2-(S)-hydroxy-5-methylhexyl ester

HRID 20354

Reaction equation

HRID 20354 reaction equation
[CH2:1]([Mg]Br)[CH:2]([CH3:4])[CH3:3].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:17][CH2:18][C@H:19]2[O:21][CH2:20]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[OH:21][C@@H:19]([CH2:20][CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:18][O:17][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-HCID 178418816HCID 178418816, compound

Product 1

HCID 87498269Toluene-4-sulfonic acid 2-(S)-hydroxy-5-methylhexyl esterYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

Add dropwise over 5 minutes isobutylmagnesium bromide (4.4 mL, 8.8 mmol, 2 M in diethyl ether) to a solution of lithium tetrachlorocuprate (4.4 mL, 0.44 mmol, 0.1 M in tetrahydrofuran) cooled to −35-40° C. Dissolve (2S)-(+)-glycidyl tosylate (1.674 g, 7.73 mmol) in tetrahydrofuran (8 mL), cool to −40° C. and cannulate into the stirring Grignard reaction flask. Quench with saturated aqueous ammonium chloride (25 mL), pour supernate into saturated aqueous ammonium chloride (25 mL) and water and shake well. Wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes) to give the desired compound (1.6711 g, 75%).

Workup

  1. customcannulate into the stirring Grignard reaction flask
  2. customQuench with saturated aqueous ammonium chloride (25 mL)
  3. additionpour supernate into saturated aqueous ammonium chloride (25 mL) and water
  4. washWash with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 10:90 to 25:75 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-3e73c66220eb47a0913b0234fe1c8597
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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