p-Toluenesulfonic acid → HCID 67300444, compound

HRID 1015510Notes

Reaction equation

HRID 1015510 reaction equation
[CH2:1]([O:8][CH2:9][C:10]12[CH2:18][CH:14]3[CH2:15][CH:16]([CH2:17]1)[C:12]([C:19]1([CH3:24])OCC[O:20]1)([CH2:13]3)[CH2:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:8][CH2:9][C:10]12[CH2:18][CH:14]3[CH2:15][CH:16]([CH2:17]1)[C:12]([C:19](=[O:20])[CH3:24])([CH2:13]3)[CH2:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59374972HCID 59374972, compound

Product 1

HCID 67300444HCID 67300444, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[1-(benzyloxymethyl)tricyclo[3.3.1.03,7]non-3-yl]-2-methyl-1,3-dioxolane (2.6 g, 7.9 mmol), p-toluenesulfonic acid (0.3 g, 1.6 mmol), and acetone (31.6 mL) was refluxed for 4 h. The volatiles were removed under vacuum and the residue was diluted with EtOAc, washed with 10% aq. NaHCO3 and brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain 1-{1-[(benzyloxy)methyl]tricyclo[3.3.1.03,7]non-3-yl}ethanone (2.1 g) as a viscous liquid in 93% yield. m/z (M+1) 285; 1H NMR (CDCl3) 300 MHz δ 7.40-7.22 (m, 5H), 4.50 (s, 2H), 3.27 (s, 2H), 2.70-2.62 (m, 1H), 2.47-2.40 (m, 1H), 2.16 (s, 2H), 2.0-1.90 (m, 2H), 1.81-1.56 (m, 7H), 1.50 (dd, J=3.0, 11.0 Hz, 1H).

Workup

  1. temperaturewas refluxed for 4 h
  2. customThe volatiles were removed under vacuum
  3. additionthe residue was diluted with EtOAc
  4. washwashed with 10% aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0b43a74c6ff4477e9c83d718001aef29
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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