Hydrochloric Acid → HCID 19858084, compound

HRID 2073401Notes

Reaction equation

HRID 2073401 reaction equation
[OH:1][CH:2]([C:7]1[CH:19]=[C:18]2[C:10]([CH:11]=[CH:12][C:13]3[O:14][C:15](=[O:22])[C:16]([CH3:21])([CH3:20])[C:17]=32)=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].N1C=CC=CC=1.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30].Cl>O>[CH3:21][C:16]1([CH3:20])[C:15](=[O:22])[O:14][C:13]2[CH:12]=[CH:11][C:10]3[C:18]([C:17]1=2)=[CH:19][C:7]([CH:2]([O:1][S:29]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30])[C:3]([F:4])([F:6])[F:5])=[CH:8][CH:9]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 19858085HCID 19858085, compound

Product 1

HCID 19858084HCID 19858084, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8-(1-hydroxy-2,2,2-trifluoroethyl)-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone (0.04 g), pyridine (0.5 ml) and tosyl chloride (0.04 g) was stirred at room temperature for 18 h and then heated at 50° for 6 h. The mixture was cooled to room temperature, treated with water (10 ml) and the mixture was stirred at room temperature for 5 minutes and acidified with 2N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was dried and evaporated to dryness under reduced pressure to give the required starting material, 1,1-dimethyl-8-(2,2,2-trifluoro-1-tosyloxyethyl)-2(1H)-naphtho[2,1-b]furanone, which was used without further purification. ##STR3##

Workup

  1. temperatureheated at 50° for 6 h
  2. temperatureThe mixture was cooled to room temperature
  3. stirringthe mixture was stirred at room temperature for 5 minutes
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe extract was dried
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4e0692dcad9d4e9d8d3fd31c1519e1a4
Source dataset
uspto-grants-1990_04
Patent number
US04916148

Reaction notes

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