Hydrochloric Acid → HCID 13590274, compound

HRID 845487Notes

Reaction equation

HRID 845487 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:17][CH:16]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37]Cl)=[CH:31][CH:30]=1.Cl>O1CCCC1.CCCCCC>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][CH2:37][CH:23]([CH2:22][CH2:21][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=2)[C:24]([OH:26])=[O:25])=[CH:31][CH:30]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 782804-(4-Methoxyphenyl)butyric acidHCID 38754101-(3-Chloropropyl)-4-methoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 13590274HCID 13590274, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisopropylamine (15 g, 0.148 mol) in dry tetrahydrofuran (100 ml) at -78° C. was treated dropwise with a solution of butyl lithium in hexane (100 ml of a 1.6M solution 0.16 mol) under an atmosphere of dry argon. The solution was allowed to warm up to 0° C. over 2 hours, cooled back to -78° C. and treated with a solution of 4-(4-methoxyphenyl)butyric acid (14.1 g, 0.0726 mol) in dry tetrahydrofuran (50 ml). The solution was allowed to warm up to -20° C., cooled back to -78° C. and treated dropwise over 2 hours with 3-(4-methoxyphenyl)propyl chloride (13.5 g, 0.0731 mol). The solution was allowed to warm up to room temperature, poured into excess 2N hydrochloric acid and extracted with chloroform. The combined extracts were dried (MgSO4) and the solvent was evaporated off under reduced pressure to give the crude product, which was further purified by column chromatography (silica gel, 50% chloroform in hexane) to give 5-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)ethyl]pentanoic acid as a colourless crystalline solid, m.p. 91°-94° C. (from toluene).

Workup

  1. temperaturecooled back to -78° C.
  2. temperatureto warm up to -20° C.
  3. temperaturecooled back to -78° C.
  4. temperatureto warm up to room temperature
  5. extractionextracted with chloroform
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customthe solvent was evaporated off under reduced pressure
  8. customto give the crude product, which
  9. customwas further purified by column chromatography (silica gel, 50% chloroform in hexane)

Sources & evidence

ORD record
ord-35a6e046ef3d400b89fdc35f6c83535e
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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