Acetic Acid → HCID 66908116, compound

HRID 1691540Notes

Reaction equation

HRID 1691540 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=2)=[C:9]([CH3:22])[CH:8]=1)[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:32][CH:31]2[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:26]([F:38])[CH:25]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:23][C:24]3[CH:29]=[CH:28][C:27]([CH:30]4[CH2:32][CH:31]4[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:26]([F:38])[CH:25]=3)[CH:15]=2)=[C:9]([CH3:22])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 231117224'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehydeHCID 59364058Ethyl 2-(4-amino-2-fluorophenyl)cyclopropane-1-carboxylate

Product 1

HCID 66908116HCID 66908116, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4′-(2-ethoxyethoxy)-2′,6′-dimethyl-3-biphenylcarbaldehyde (0.313 g, 1.05 mmol), ethyl 2-(4-amino-2-fluorophenyl)cyclopropanecarboxylate (0.234 g, 1.05 mmol), acetic acid (0.126 g, 2.10 mmol) and 1,2-dichloroethane (5 mL) was stirred under a nitrogen atmosphere at room temperature for 3 hr. Sodium triacetoxyborohydride (0.445 g, 2.10 mmol) was added to the reaction mixture by small portions, and the mixture was stirred for 3.5 hr. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-30:70) to give the title compound (0.456 g, yield 86%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred for 3.5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-30:70)

Sources & evidence

ORD record
ord-b5ddb9abaaeb432b9bf4fab26363443d
Source dataset
uspto-grants-2012_04
Patent number
US08153694B2

Reaction notes

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