Sodium hydride → 3-Methyl-2-butenyl 2'-fluoro-2-(((3-methyl-2-butenyl)oxy)methyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662481Notes

Reaction equation

HRID 1662481 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH2:20][OH:21].[H-].[Na+].Br[CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][CH:2]=[C:3]([CH3:10])[CH3:4])=[O:17])=[CH:12][C:11]=1[CH2:20][O:21][CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 57707070Methyl 2'-fluoro-2-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 577064623-Methyl-2-butenyl 2'-fluoro-2-(((3-methyl-2-butenyl)oxy)methyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 66.63A (0.322 mmol) in DMF (4 mL), was added NaH (0.0100 g, 0.419 mmol). The resulting mixture was stirred at room temperature for 10 minutes. 1-Bromo-3-methylbut-2-ene (0.240 g, 1.61 mmol) (commercially available from Aldrich) was added and the mixture was stirred at room temperature for 2 hours. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:6 EtOAc/hexane) and gave 67.27A as a colorless oil, in 77% yield. MS ESI (pos.) m/e: 430 (M+18)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customAfter removing solvent
  3. customthe residue was purified by flash chromatography (silica gel, 1:6 EtOAc/hexane)

Sources & evidence

ORD record
ord-ca79c9a0e5704da0845a1c358da350f8
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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