Hydrochloric Acid → HCID 59188719, compound

HRID 2090517Notes

Reaction equation

HRID 2090517 reaction equation
[F:1][C:2]([F:25])([C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3](Cl)=[O:4].[OH:26][C:27]1[CH:69]=[CH:68][C:30]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:44]4[CH:43]=[CH:42][C:41]([C:62]5[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=5)([C:51]5[CH:56]=[CH:55][C:54]([N:57]6[CH2:61][CH2:60][CH2:59][CH2:58]6)=[CH:53][CH:52]=5)[O:40][C:39]=4[CH:38]=3)=[CH:33][CH:32]=2)=[CH:29][CH:28]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[F:1][C:2]([F:25])([C:6]([F:24])([F:23])[C:7]([F:22])([F:21])[C:8]([F:20])([F:19])[C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:3]([O:26][C:27]1[CH:28]=[CH:29][C:30]([C:31]2[CH:32]=[CH:33][C:34]([C:37]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:44]4[CH:43]=[CH:42][C:41]([C:62]5[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=5)([C:51]5[CH:56]=[CH:55][C:54]([N:57]6[CH2:61][CH2:60][CH2:59][CH2:58]6)=[CH:53][CH:52]=5)[O:40][C:39]=4[CH:38]=3)=[CH:35][CH:36]=2)=[CH:68][CH:69]=1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 78978Perfluorooctanoyl chlorideHCID 70862872HCID 70862872, compound

Product 1

HCID 59188719HCID 59188719, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluoro-octanoyl chloride (0.30 g, 0.7 mmol) was added to a solution of 6-[4′-(hydroxy)biphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[2,1-b]pyran (0.40 g, 0.7 mmol) in DCM (30 mL) containing pyridine (2 mL) under N2 at 0° C. with stirring. The mixture was stirred at room temperature for 1 h, poured into HCl (2 M, 100 mL), extracted with DCM (3×50 mL), washed with water (100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (60% in hexanes) as eluent and the solvent removed under reduced pressure. The residue was dissolved in Et2O, hexane was added and the solvent reduced. The resulting precipitate was filtered to give the title compound (0.17 g, 25%) as a colourless powder, mp 144-145° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. extractionextracted with DCM (3×50 mL)
  3. washwashed with water (100 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. filtrationThe residue was filtered through a short plug of silica
  7. customthe solvent removed under reduced pressure
  8. dissolutionThe residue was dissolved in Et2O
  9. additionhexane was added
  10. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-8c70e3de90e547eb8572cc707ff9ceb2
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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