Trifluoroacetic acid → HCID 56840609, compound

HRID 1913484Notes

Reaction equation

HRID 1913484 reaction equation
C(O)(C(F)(F)F)=O.[O:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[C:15]([C:18](=[O:36])[CH2:19][CH2:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29]COCCOC)=[CH:25][CH:24]=3)=[O:22])[CH:16]=[CH:17][C:9]1=2>C(Cl)Cl>[O:8]1[CH2:13][CH2:12][O:11][C:10]2[CH:14]=[C:15]([C:18](=[O:36])[CH2:19][CH2:20][C:21]([C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)=[O:22])[CH:16]=[CH:17][C:9]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56840388HCID 56840388, compound

Product 1

HCID 56840609HCID 56840609, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat TFA (0.5 mL) was added to a solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-(4-((2-methoxyethoxy)methoxy)phenyl)butane-1,4-dione 11 (0.35 mmol) in CH2Cl2 (5 mL) stirred at room temperature. The solution was further stirred overnight at room temperature. The volatiles were evaporated under vacuum. The residue was purified by flash chromatography over silica gel eluting with 1% methanol in CH2Cl2 to get 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-(4-hydroxyphenyl)butane-1,4-dione 4 as an off white solid (21% yield). 1H NMR (CDCl3, 400 MHz): δ ppm 3.37 (m, 4H), 4.29 (m, 2H), 4.33 (m, 2H), 5.76 (s, 1H), 6.87 (d, J=8.8 Hz, 2H), 6.93 (m, 1H), 7.60 (m, 2H), 7.94 (d, J=8.8 Hz, 2H); ESIMS found C18H16O5 m/z 313 (M+H).

Workup

  1. customThe volatiles were evaporated under vacuum
  2. customThe residue was purified by flash chromatography over silica gel eluting with 1% methanol in CH2Cl2

Sources & evidence

ORD record
ord-f057361fc7d7439a9060bf219989809f
Source dataset
uspto-grants-2013_12
Patent number
US08609717B2

Reaction notes

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