Water → 3-[(3-Chlorophenyl)ethynyl]-1,9,13-trioxa-2-azadispiro[4.2.5.2]pentadec-2-ene

HRID 2040884Notes

Reaction equation

HRID 2040884 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:21](O)[CH2:22][CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH2:14][C:13]3([CH2:19][CH2:18][C:17]4([O:24][CH2:23][CH2:22][CH2:21][O:20]4)[CH2:16][CH2:15]3)[O:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 104421,3-PropanediolHCID 566464673-[(3-Chlorophenyl)ethynyl]-1-oxa-2-azaspiro[4.5]dec-2-en-8-one

Product 1

HCID 566444343-[(3-Chlorophenyl)ethynyl]-1,9,13-trioxa-2-azadispiro[4.2.5.2]pentadec-2-eneYield 75.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the compound of Example 32 (0.41 g, 1.42 mmol), 1,3-propandiol (0.15 g, 1.95 mmol) and p-toluensulfonic acid. H2O (7.5 mg, 0.04 mmol) in 30 mL of benzene was stirred at reflux for 10.5 h, removing water with a Dean-Stark Apparatus. Dilution with water, washing with aq. 5% NaHCO3, drying the organic layer over Na2SO4 afforded the title compound as dense yellow oil. This was further purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 9:1 to 7:3) giving a white solid. Yield: 75.3%.

Workup

  1. temperatureat reflux for 10.5 h
  2. customremoving water with a Dean-Stark Apparatus
  3. washDilution with water, washing with aq. 5% NaHCO3
  4. dry with materialdrying the organic layer over Na2SO4

Sources & evidence

ORD record
ord-d0bc22ea6457413e94f6946d7b902459
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

Loading…