Hydrochloric Acid → HCID 66869542, compound

HRID 1992631Notes

Reaction equation

HRID 1992631 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1(O)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[Cl:18])[CH3:2].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.Cl>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][C:7]=1[Cl:18])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67749Trifluoromethanesulfonic anhydrideHCID 66869283HCID 66869283, compound

Product 1

HCID 66869542HCID 66869542, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

(2-Chloro-1-hydroxy-7-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetic acid ethyl ester (42.7 g, 142.9 mmol) is dissolved under an atmosphere of argon in pyridine (250 ml). Trifluoromethanesulfonic acid anhydride (30.7 ml, 185.8 mmol) is added during 30 minutes, while keeping the temperature at 25° C. with occasional cooling with a ice bath. After addition is complete, the reaction mixture is warmed to 50° C. for 2 h. TLC analysis indicates complete conversion of starting material. 2 M aqueous HCl (100 ml) is carefully added, and then the reaction mixture is concentrated to dryness on the rotary evaporator. The residue is taken up in 2 M aqueous HCl (100 ml) and extracted with EtOAc. The organic layer is dried over Na2SO4 and concentrated. Purification by FCC (EtOAc) affords the title compound. ES+−MS: 281.2, 283.2 [M+H]+.

Workup

  1. customat 25° C.
  2. temperaturewith occasional cooling with a ice bath
  3. additionAfter addition
  4. concentrationthe reaction mixture is concentrated to dryness on the rotary evaporator
  5. extractionextracted with EtOAc
  6. dry with materialThe organic layer is dried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by FCC (EtOAc)

Sources & evidence

ORD record
ord-31ff7647d02e4da3b36cd6d6fe6f4a38
Source dataset
uspto-grants-2010_01
Patent number
US07648989B2

Reaction notes

Loading…