Water → HCID 11725738, compound

HRID 1836710Notes

Reaction equation

HRID 1836710 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]([OH:22])[CH:20]=[CH2:21])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31].O>ClCCl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]([O:22][C:30](=[O:32])[CH3:31])[CH:20]=[CH2:21])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 99957151-(1-Benzenesulfonyl-1H-indol-2-yl)-allyl alcohol

Product 1

HCID 11725738HCID 11725738, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
3 °C

Procedure

To a solution of 19.1 g of 1-(1-benzenesulfonyl-1H-indol-2-yl)-allyl alcohol (74 mmol) in 244 ml dichloromethane were added 34 ml triethylamine and 0.7 g 4-dimethyl-aminopyridine. The solution was cooled to 3° C. To the magnetically stirred solution 23.5 ml of acetic anhydride qas added with a dropping funnel at a temperature below 5° C. The reaction mixture was stirred 2 h at 22° C. After cooling in an ice bath 250 ml of water was added at a temperature of 20 to 24° C. The mixture was vigorously stirred for 10 min. The phases were separated, and the water solution extracted with 250 ml of dichloromethane. The combined organic phases were extracted with 250 ml of water three times, and once with 250 ml of brine. The dichloromethane solution was dried on sodium sulfat and finally rotary evaporated (35° C., 50 mbar), yield 22.8 g. In the next step (the cyclocarbonylation) the resulting oil was used without purification (crude quality).

Workup

  1. additionwas added at a temperature of 20 to 24° C
  2. stirringThe mixture was vigorously stirred for 10 min
  3. customThe phases were separated
  4. extractionthe water solution extracted with 250 ml of dichloromethane
  5. extractionThe combined organic phases were extracted with 250 ml of water three times
  6. dry with materialThe dichloromethane solution was dried on sodium sulfat
  7. customfinally rotary evaporated (35° C., 50 mbar), yield 22.8 g
  8. customIn the next step (the cyclocarbonylation) the resulting oil was used without purification (crude quality)

Sources & evidence

ORD record
ord-418803d0a67e4eb48a3f8fdce240e1d9
Source dataset
uspto-grants-2004_08
Patent number
US06777559B2

Reaction notes

Loading…