Water → HCID 14027479, compound

HRID 444416Notes

Reaction equation

HRID 444416 reaction equation
[CH3:1][C:2](=[CH2:7])[CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[S:15](Cl)([CH3:18])(=[O:17])=[O:16].O>C(Cl)Cl>[CH3:18][S:15]([O:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:1])=[CH2:7])(=[O:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 897374-Methylpent-4-ene-1-ol

Product 1

HCID 14027479HCID 14027479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-4-penten-1-ol (10.0 g, 0.10 mmol) is placed in 100 ml dry methylene chloride and cooled, with stirring and under nitrogen, in an acetone/dry ice bath to 0°. Triethylamine (42 ml, 0.30 mmol) is added all at once, followed by mesyl chloride (12 ml, 0.16 mmol) over a 15 min period. The mixture is stirred at 0° for 2 hr and then water is added, followed by stirring for 5 min. The mixture is worked up by extraction with water and the layers are separated. The aqueous phase is extracted with methylene chloride (2×); the organic layers are combined and washed with sat. NaHCO3, 2 N HCl, water and brine, dried over MgSO4, filtered and evaporated (not to dryness), giving 4-methyl-4-pentenyl methanesulfonate.

Workup

  1. temperaturecooled
  2. stirringThe mixture is stirred at 0° for 2 hr
  3. stirringby stirring for 5 min
  4. extractionThe mixture is worked up by extraction with water
  5. customthe layers are separated
  6. extractionThe aqueous phase is extracted with methylene chloride (2×)
  7. washwashed with sat. NaHCO3, 2 N HCl, water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated (not to dryness),

Sources & evidence

ORD record
ord-02e043e1b85f49ffadac3edfdd9e30f0
Source dataset
uspto-grants-1981_04
Patent number
US04264518

Reaction notes

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