Hydrochloric Acid → HCID 22668865, compound

HRID 395410Notes

Reaction equation

HRID 395410 reaction equation
[C:1]([CH:3]([C:7]1[C:8]([CH2:24][CH:25]2[CH2:27][CH2:26]2)=[C:9]([C:20]([O:22][CH3:23])=[O:21])[C:10]([CH:17]([F:19])[F:18])=[N:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[CH2:4][CH:5]=[CH2:6])#N.[H-].C([Al+]CC(C)C)C(C)C.Cl.CC[O:41]CC>>[CH:25]1([CH2:24][C:8]2[C:7]([CH:3]([CH:1]=[O:41])[CH2:4][CH:5]=[CH2:6])=[C:12]([C:13]([F:15])([F:16])[F:14])[N:11]=[C:10]([CH:17]([F:18])[F:19])[C:9]=2[C:20]([O:22][CH3:23])=[O:21])[CH2:26][CH2:27]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21225700DiisobutylaluminumhydrideHCID 22668795HCID 22668795, compound

Product 1

HCID 22668865HCID 22668865, compound

Procedure

To a solution of 16.5 g(68.3 mmol) of methyl 5-(1-cyano-3-butenyl)-4-(cyclopropylmethyl)-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridine-carboxylate (example 16 of U.S. Pat. No. 5,169,432) in 250 ml of ether cooled in an ice bath was added 91 ml (136 mmol) of diisobutylaluminum hydride (1.5 M in toluene). The reaction mixture was stirred on an ice bath for 30 min and was treated with 200 ml of 2.4 M HCl. The organic layer was washed with brine, dried (MgSO4), and filtered through silica gel. The filtrate was concentrated in vacuo and the residue was purified by HPLC (17% EtOAc in hexane) to give 8.1 g of methyl 4-(cyclopropylmethyl)-2-(difluoromethyl)-5-(1-formyl-3-butenyl)-6-(trifluoromethyl)-3-pyridinecarboxylate.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered through silica gel
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by HPLC (17% EtOAc in hexane)

Sources & evidence

ORD record
ord-019de4c65d534e2089588bd247e32c86
Source dataset
uspto-grants-2003_08
Patent number
US06605624B1

Reaction notes

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