Oxiranemethanol, 3-[(phenylmethoxy)methyl]- → 3-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

HRID 400233

Reaction equation

HRID 400233 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[O:14][CH:11]1[CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([Mg]Cl)[CH:16]=[CH2:17]>O1CCCC1>[CH2:17]([C:10]([OH:14])([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][CH2:12][OH:13])[CH:16]=[CH2:15]

Participants

4

Reactant 2

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-HCID 178418473HCID 178418473, compound

Product 1

HCID 189441063-Allyl-4-(benzyloxy)-3-hydroxy-1-butanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

A solution of 4-benzyloxy-2,3-epoxy-1-butanol (6.28 g, 32.37 mmol) in anhydrous tetrahydrofuran (75 mL) was added dropwise at -40° C. over a period of 45 minutes, to a 2M solution of allyl magnesium chloride (48.5 mL, 97 mmol) and tetrahydrofuran (50 mL). The solution was stirred at -40° C. for 1 hour, warmed to 0° C. and quenched by addition of aqueous ammonium chloride solution. The tetrahydrofuran layer was separated and the aqueous layer was extracted with ethyl acetate (three times). The combined organic extract was dried (magnesium sulfate), filtered and concentrated to obtain a mixture of compounds A and B.

Workup

  1. temperaturewarmed to 0° C.
  2. customquenched by addition of aqueous ammonium chloride solution
  3. customThe tetrahydrofuran layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (three times)
  5. extractionThe combined organic extract
  6. dry with materialwas dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain

Sources & evidence

ORD record
ord-757e5a1c8b554ab7918a14250606dd48
Source dataset
uspto-grants-1998_10
Patent number
US05827868

Linked notes

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