Hydrochloric Acid → 3-(4-fluorophenyl)-6-(4'-(hexanoyloxy)biphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

HRID 2090519Notes

Reaction equation

HRID 2090519 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:21][C:20]3[CH:22]=[C:23]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)[C:24]4[C:29]([C:19]=3[CH:18]=[CH:17]2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:12][CH:11]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:21][C:20]3[CH:22]=[C:23]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[CH:41]=[CH:40][C:39]([O:42][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:38][CH:37]=5)=[CH:32][CH:31]=4)[C:24]4[C:29]([C:19]=3[CH:18]=[CH:17]2)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67340Hexanoyl chloride2×HCID 591887153-(4-fluorophenyl)-6-(4'-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

Product 1

HCID 591887093-(4-fluorophenyl)-6-(4'-(hexanoyloxy)biphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyranYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hexanoyl chloride (5.01 g, 37 mmol) was added dropwise to a solution of 3-(4-fluorophenyl)-6-(4′-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran (19.37 g, 37 mmol) in DCM (100 mL) containing pyridine (20 mL) at 0° C. After ½ h additional hexanoyl chloride (5.01 g, 37 mmol) was added. Stirring was continued for a further ½ h more, the solution was poured into HCl (2 M, 400 mL), separated and extracted with DCM (2×100 mL), the combined organic phases were washed with water saturated sodium bicarbonate (200 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (50% in hexanes) as eluent. The solvent was removed under reduced and the residue triturated alternately with hexanes and methanol twice. The residue was dried under vacuum to give the title compound (16.51 g, 72%) as a yellow foam, mp 64-65° C.

Workup

  1. customseparated
  2. extractionextracted with DCM (2×100 mL)
  3. washthe combined organic phases were washed with water saturated sodium bicarbonate (200 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 was removed
  8. customthe residue triturated alternately with hexanes and methanol twice
  9. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-eadfda23f1194b3a93e05f3a44c3dc95
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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