Methyl chloroformate → Methyl 3-[4-(4-pentylphenyl)phenyl]propionate

HRID 1386579Notes

Reaction equation

HRID 1386579 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([N-]CC(C)C)C(C)C.[Li+].Cl[C:31]([O:33][CH3:34])=[O:32]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][C:31]([O:33][CH3:34])=[O:32])=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 3

HCID 6586Methyl chloroformateHCID 34468404-Ethynyl-4'-pentyl-1,1'-biphenylHCID 11018925Lithium diisobutylamide

Product 1

HCID 21182420Methyl 3-[4-(4-pentylphenyl)phenyl]propionate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-Pentylphenyl)phenylacetylene (2.09 g) in tetrahydrofuran (30 ml) was added dropwise a solution of lithium diisobutylamide in a mixture of tetrahydrofuran and n-hexane (1.60 M, 5.6 ml) at −75° C., and the resultant mixture was stirred for an hour at −78° C. To the mixture was added methyl chloroformate (0.72 ml), and the reaction mixture was allowed to warm to ambient temperature. The solution was diluted with ethyl acetate, and washed in turn with water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude product, which was subjected to column chromatography on silica gel (150 ml), and eluted with a mixture of (n-hexane:ethyl acetate=100:0-9:1, V/V) to give Methyl 3-[4-(4-pentylphenyl)phenyl]propionate (2.20 g).

Workup

  1. washwashed in turn with water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. customto give a crude product, which
  6. washeluted with a mixture of (n-hexane:ethyl acetate=100:0-9:1, V/V)

Sources & evidence

ORD record
ord-43b71c45f5744d19bdbfffbd18270e4f
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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