p-Toluenesulfonic acid → HCID 59971325, compound

HRID 381624Notes

Reaction equation

HRID 381624 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C@@H:8](O)[CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@H:8]2[O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 59904767HCID 59904767, compound

Product 1

HCID 59971325HCID 59971325, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl (S)-6-(4-fluorophenoxy)-5-hydroxy-hexanoate (0.8 g 3.12 mmol) in CH2Cl2 (20 ml), a catalytic amount of PTSA (10 mg) was added and the reaction mixture was stirred at 40° C. for 12 h. The reaction was then neutralised with sodium bicarbonate and the product extracted with dichloromethane. The organic layer was dried (Na2SO4) and concentrated. The crude product on purification on a silica gel (EtOAc-light petroleum (1:3) as eluent) gave (6S)-6-(4-fluorophenoxymethyl)-tetrahydropyran-2-one (0.5 g, 70%) as a colourless liquid. TLC:ethyl acetate-light petroleum (1:4), Rf=0.3. Optical rotation [α]D: +19° (c 0.9, CHCl3). 1H NMR (CDCl3, 200 MHz): δ 1.7-2.15 (m, 4H), 2.48-2.7 (m, 2H), 3.95-4.15 (m, 2H), 4.55-4.7 (m, 1H), 6.77-7.0 (m, 4H).

Workup

  1. extractionthe product extracted with dichloromethane
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product on purification on a silica gel (EtOAc-light petroleum (1:3) as eluent)

Sources & evidence

ORD record
ord-d36fa781e6ce4e77916cfb11c3b24485
Source dataset
uspto-grants-2001_10
Patent number
US06306895B1

Reaction notes

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