Triethylamine → Methanesulfonic acid 2-phenyl-allyl ester

HRID 77327

Reaction equation

HRID 77327 reaction equation
[C:1]1([C:7](=[CH2:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[C:1]1([C:7](=[CH2:10])[CH2:8][O:9][S:19]([CH3:18])(=[O:21])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 80106beta-Methylenephenethyl alcohol

Product 1

HCID 86653276Methanesulfonic acid 2-phenyl-allyl esterYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a well stirred solution of 2-phenyl-prop-2-en-1-ol (700 mg, 5.22 mmol) in dichlorometane (10 mL) at 0° C. is added triethylamine (0.945 mL, 6.78 mmol) and methylsulfonyl chloride (0.424 mL, 5.48 mmol). The reaction is allowed to stir for 10 min, warmed to room temperature and is stirred for 30 min. The reaction is quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate. The organic layers are combined, washed with 1 N hydrochloric acid, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (10% ethyl acetate in hexanes) to yield the title compound (1.07 g, 4.95 mmol).

Workup

  1. stirringis stirred for 30 min
  2. customThe reaction is quenched by the addition of a saturated aqueous solution of ammonium chloride
  3. extractionextracted several times with ethyl acetate
  4. washwashed with 1 N hydrochloric acid, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified via silica gel chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-70d466be53c046c28b3842119842f724
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Linked notes

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