Water → HCID 12756316, compound

HRID 1907015Notes

Reaction equation

HRID 1907015 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:22][CH3:23])([O:20][CH3:21])[CH:17]([OH:19])[CH3:18])=[CH:12][CH:11]=1)[CH:7]([CH3:9])[CH3:8].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:1][S:2]([O:19][CH:17]([CH3:18])[C:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:6][CH:7]([CH3:9])[CH3:8])=[CH:11][CH:12]=1)([O:22][CH3:23])[O:20][CH3:21])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 13504793HCID 13504793, compound

Product 1

HCID 12756316HCID 12756316, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.25 g of methanesulfonyl chloride in 20 ml of dry methylene chloride is added dropwise to a mixture of 12.37 g of 1-(4-isobutylphenyl)-1,1-dimethoxypropan-2-ol and 80 ml of dry methylene chloride containing 6.5 g of dry triethylamine at 5°-10° C. The addition takes place over about 40 minutes and the reaction mixture is stirred for an additional 1.5 hours at 5°-10° C. after that addition is completed. After that time, an additional 0.6 g of methanesulfonyl chloride is added at 5°-10° C. and stirring is continued for an additional 50 minutes. An additional 1.5 g of triethylamine is added to the reaction mixture and then the reaction mixture is poured into 50 ml of water. The aqeuous and organic phases are separated and the aqueous phase is extracted with methylene chloride. The combined methylene chloride layers then are washed with 50 ml of saturated aqueous sodium chloride and the methylene chloride layer is dried over sodium sulfate. After filtration to remove the sodium sulfate, the methylene chloride is evaporated on a rotary evaporator under reduced pressure to afford 1-(4-isobutylphenyl)-1,1-dimethoxyprop-2-yl methanesulfonate [which is characterized by an NMR spectra in deuterochloroform of τ=9.10 (doublet, J=2.2), 8.8 (doublet, J=2.1), 8.12 (septet, J=2.1), 7.48 (doublet, J=2.3), 6.88, 6.75, 6.67, 4.92 (quartet, J=2.1) and 2.5-2.9 (aromatic AB pattern)].

Workup

  1. additionThe addition
  2. customover about 40 minutes
  3. additionafter that addition
  4. stirringstirring
  5. waitis continued for an additional 50 minutes
  6. customThe aqeuous and organic phases are separated
  7. extractionthe aqueous phase is extracted with methylene chloride
  8. washThe combined methylene chloride layers then are washed with 50 ml of saturated aqueous sodium chloride
  9. dry with materialthe methylene chloride layer is dried over sodium sulfate
  10. filtrationAfter filtration
  11. customto remove the sodium sulfate
  12. customthe methylene chloride is evaporated on a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-3a68afdc95eb490eb914c8269e39372f
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

Loading…