Water → HCID 72483449, compound

HRID 2220571Notes

Reaction equation

HRID 2220571 reaction equation
[CH2:1]([O:3][C:4]1[CH:28]=[CH:27][C:7]2[CH:8]3[CH2:14][CH2:13][C:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([F:25])[C:17]=4[F:26])(O)[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:29])[CH3:2].O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:28]=[CH:27][C:7]2[CH:8]3[CH2:14][CH:13]=[C:12]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([F:25])[C:17]=4[F:26])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:29])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 68447641HCID 68447641, compound

Product 1

HCID 72483449HCID 72483449, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.5 g (20.8 mmol) of (±)-(4aR*, 9bS*)-7-ethoxy-3-(4-ethoxy-2,3-difluorophenyl)-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-ol in 200 ml of toluene are heated on a water separator for 30 min together with 396 mg (2.08 mmol) of p-toluenesulfonic acid monohydrate. After cooling, the batch is filtered adsorptively (SiO2, ethyl acetate:n-heptane=4:1), and the filtrate is concentrated to dryness. The product mixture obtained in this way can be used directly for the following reaction.

Workup

  1. temperatureAfter cooling
  2. filtrationthe batch is filtered adsorptively (SiO2, ethyl acetate:n-heptane=4:1)
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe product mixture obtained in this way
  5. customcan be used directly for the following reaction

Sources & evidence

ORD record
ord-44206f04112b4440b5866f4e490e301c
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

Loading…