p-Toluenesulfonic acid monohydrate → HCID 91557505, compound

HRID 1772400Notes

Reaction equation

HRID 1772400 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([C:17]1[CH:18]=[C:19]([C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH2:29][CH:30]([CH3:37])[CH:31]3O)[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)([CH3:16])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[C:13]([C:17]1[CH:18]=[C:19]([C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH2:29][C:30]([CH3:37])=[CH:31]3)[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117817947HCID 117817947, compound

Product 1

HCID 91557505HCID 91557505, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid monohydrate (1.57 g, 8.26 mmol, 0.2 equiv), compound 10 (15 g crude, ˜41.32 mmol, 1.0 equiv) and toluene (300 mL) was refluxed for 1 hour. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified over silica gel (300 g) eluting with heptanes to give compound 11 (10.8 g, 82% overall yield for 2 steps) as a white solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. washthe mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified over silica gel (300 g)
  7. washeluting with heptanes

Sources & evidence

ORD record
ord-2be793fb316d4b619b60500381356197
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

Loading…