Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 1-(Hydroxymethyl)cyclopropyl acetate

HRID 1517874Notes

Reaction equation

HRID 1517874 reaction equation
[C:1]([O:4][C:5]1([CH2:8][O:9]C2CCCCO2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[C:1]([O:4][C:5]1([CH2:8][OH:9])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 666697401-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl acetate

Product 1

HCID 666698221-(Hydroxymethyl)cyclopropyl acetateYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl acetate (149 mg, 0.696 mmol) in 10 mL of methanol was added PPTS (18 mg, 0.07 mmol, Aldrich) in portions. After stirring for 5 hrs at rt, the mixture was quenched with 10 mL of water and extracted with dichloromethane (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE: EtOAc=10:1) to give the title compound as pale yellow oil (46 mg, 35.5%).

Workup

  1. customthe mixture was quenched with 10 mL of water
  2. extractionextracted with dichloromethane (20 mL×3)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE: EtOAc=10:1)

Sources & evidence

ORD record
ord-cede4d9776f64e9b92e3cfaeaec3f6ba
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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