Water → 1-{[3-(Methyloxy)phenyl]methyl}propyl methanesulfonate

HRID 1992847Notes

Reaction equation

HRID 1992847 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([OH:13])[CH2:11][CH3:12])[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(Cl)Cl>[CH3:21][S:22]([O:13][CH:10]([CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:11][CH3:12])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 612614231-(3-Methoxyphenyl)butan-2-ol

Product 1

HCID 866166461-{[3-(Methyloxy)phenyl]methyl}propyl methanesulfonateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-[3-(Methyloxy)phenyl]-2-butanol (51) (3.50 g, 19.4 mmol) was dissolved in CH2Cl2 (90 mL). To this solution was added Et3N (5.4 mL, 38.8 mmol) followed by catalytic amount of N,N-dimethylaminopyridine (DMAP). The mixture was cooled in an ice bath, methanesulfonyl chloride (2.3 mL, 29.1 mmol) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred at room temperature overnight. Water was added to the mixture, CH2Cl2 layer was separated. The aqueous layer was further extracted with CH2Cl2 (50 mL). The extracts were combined and washed with brine, (Na2SO4), filtered, and the filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (4:1) to give 4.66 g (94%) of the title compound (52) as a yellow oil, which solidified upon freezing. 1H NMR (400 MHz, CDCl3): δ 1.03 (t, J=7.5 Hz, 3H), 1.70-1.85 (m, 2H), 2.53 (s, 3H), 2.94 (d, J=6.7 Hz, 2H), 3.80 (s, 3H), 4.70-4.80 (m, 1H), 6.75-6.85 (m, 3H), 7.20-7.25 (m, 1H).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customwas separated
  3. extractionThe aqueous layer was further extracted with CH2Cl2 (50 mL)
  4. washwashed with brine, (Na2SO4),
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as a brown oil
  8. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (4:1)

Sources & evidence

ORD record
ord-a3d59f7b0dd04437954d75cee2add243
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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