p-Toluenesulfonic acid → HCID 66930311, compound

HRID 1258492Notes

Reaction equation

HRID 1258492 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]2[O:24][CH2:25]C(=O)[CH:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([O:33][CH3:34])([O:31][CH3:32])OC.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:13]2[O:24][CH2:25][C:28]([O:31][CH3:32])([O:33][CH3:34])[CH:12]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 66930122HCID 66930122, compound

Product 1

HCID 66930311HCID 66930311, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Compound 12a (7.6 g) was dissolved dry methanol (100 mL). Trimethyl orthoformate (30 mL) and pTsOH (0.2 g) was added at rt under a nitrogen atmosphere. The mixture was heated at 60° C. for 8 hours. Once the reaction was deemed complete according to TLC, it was cooled to rt and concentrated in vacuo. The crude product was purified by column chromatography over silica gel eluting with ethyl acetate-heptane (1:4) to afford after concentration in vacuo the ketal 12b as a clear oil (5.9 g, 71% over 2 steps); ESI+, m/z: 382 (M+−OMe).

Workup

  1. temperaturewas cooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography over silica gel eluting with ethyl acetate-heptane (1:4)
  4. customto afford
  5. concentrationafter concentration in vacuo the ketal 12b as a clear oil (5.9 g, 71% over 2 steps)

Sources & evidence

ORD record
ord-bf94158a85144236a03e0e94b6950970
Source dataset
uspto-grants-2013_06
Patent number
US08466158B2

Reaction notes

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