Methanesulfonyl chloride → 5-Phenyl-2-pentanol mesylate

HRID 236069Notes

Reaction equation

HRID 236069 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([OH:12])[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>O1CCCC1>[S:14]([O:12][CH:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:11])(=[O:16])(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1027884-Hydroxy-1-phenylpentane

Product 1

HCID 128783865-Phenyl-2-pentanol mesylateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-phenyl-2-pentanol (482 g.; 2.94 moles) in tetrahydrofuran (2250 ml.) at 0° C. was added methanesulfonyl chloride (300 ml.) at such a rate that the internal temperature does not rise above 10° C. (total addition time 4.5 hours). After addition is complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for an additional hour. The reaction mixture was filtered and the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) and washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.), dried (MgSO4), filtered through diatomaceous earth and concentrated to a light orange oil (687 g., 95% yield). This material was suitable for use without further purification.

Workup

  1. customdoes not rise above 10° C.
  2. addition(total addition time 4.5 hours)
  3. additionAfter addition
  4. waitwas continued for an additional hour
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe supernate concentrated to a light yellow oil (2800 g.) which
  7. dissolutionwas dissolved in chloroform (2 liters)
  8. washwashed with water (4×1 liter), brine (1×1 liter), charcoal
  9. additiontreated (50 g.)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered through diatomaceous earth
  12. concentrationconcentrated to a light orange oil (687 g., 95% yield)
  13. customThis material was suitable for use without further purification

Sources & evidence

ORD record
ord-aa3fda21598f46a38bf8163647658114
Source dataset
uspto-grants-1987_02
Patent number
US04642373

Reaction notes

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