Hexane → HCID 54026571, compound

HRID 260751

Reaction equation

HRID 260751 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].C([Li])CCC.CCCCCC.[CH2:39]([C:43]1[N:44]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[Cl:57])[C:45]([CH:48]=O)=[CH:46][N:47]=1)[CH2:40][CH2:41][CH3:42]>O1CCCC1.O>[CH2:39]([C:43]1[N:44]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[Cl:57])[C:45]([CH2:48][CH:8]=[CH:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:46][N:47]=1)[CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 4

HCID 8058HexaneHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-HCID 178418339Butyllithium

Product 1

HCID 54026571HCID 54026571, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of (4-carboxybutyl)triphenyl-phosphonium bromide (1.04 g, 2.35 mmol) in dry tetrahydrofuran (25 mL) at 0° C. under argon was added n-butyl lithium in hexane (1.8 mL of 2.5M, 4.6 mmol). The reaction mixture was stirred for 15 minutes at 0° C. and then a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde [Example 6 (iii)] (0.5 g, 1.81 mmol) in tetrahydrofuran (25 mL) was added dropwise. The mixture was stirred an additional hour at 0° C. and then at ambient temperature for 3 days. Water was added and the mixture was extracted with diethyl ether. The aqueous layer was acidified to pH 3 with aqueous hydrochloric acid solution. The product was extracted into ethyl acetate, washed with water, dried, concentrated, and chromatographed over silica gel eluting with 5-10% methanol in methylene chloride to give 0.24 g of 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-4-hexenoic acid.

Workup

  1. stirringThe mixture was stirred an additional hour at 0° C.
  2. waitat ambient temperature for 3 days
  3. extractionthe mixture was extracted with diethyl ether
  4. extractionThe product was extracted into ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customchromatographed over silica gel eluting with 5-10% methanol in methylene chloride

Sources & evidence

ORD record
ord-f292aa281dd543869c402cc2b082136b
Source dataset
uspto-grants-1996_06
Patent number
US05530017

Linked notes

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