Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 6-Fluoro-6-methylheptan-1-ol

HRID 363519Notes

Reaction equation

HRID 363519 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([F:16])([CH3:15])[CH3:14].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCO>[F:16][C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:7]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 106572356-Fluoro-6-methylheptyl 2-tetrahydropyranyl ether

Product 1

HCID 104870116-Fluoro-6-methylheptan-1-olYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of the product from Step III (3.34 g, 0.0144 mol) in absolute EtOH was treated with pyridinium p-toluenesulfonate (0.47 g, 0.00187 mol) and kept under nitrogen at ambient temperature for 41 hours. The mixture was concentrated and the residue, dissolved in EtOAc, was washed with aqueous NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 5 to 20% EtOAc-hexane to give 1.86 g of 6-fluoro-6-methyl-1-heptanol.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue, dissolved in EtOAc
  3. washwas washed with aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with 5 to 20% EtOAc-hexane

Sources & evidence

ORD record
ord-66dcfa950cf948ad94e0ccf77aff0260
Source dataset
uspto-grants-1999_02
Patent number
US05874475

Reaction notes

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