Pentanoic acid, 5-oxo-, methyl ester → HCID 13105365, compound

HRID 1981226Notes

Reaction equation

HRID 1981226 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[PH4+].C(CCCC(OC)=O)=O.[CH:16]1[C:25]2[C:20](=[CH:21]C=CC=2)[CH:19]=[CH:18][C:17]=1/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]>CCCCCC.O1CCCC1>[CH3:4][C:3]1[CH:21]=[C:20]2[C:25](=[CH:1][CH:2]=1)[CH:16]=[C:17](/[CH:26]=[CH:27]/[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:18]=[CH:19]2

Participants

7

Reactant 4

HCID 554053Pentanoic acid, 5-oxo-, methyl esterHCID 5460504PhosphoniumHCID 10729621HCID 10729621, compoundHCID 178418339Butyllithium

Product 1

HCID 13105365HCID 13105365, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

1.6M Butyl lithium solution in hexane (6.7 ml) was added to a stirred suspension of the phosphonium salt (5.0 g) in dry tetrahydrofuran (50 ml) at 5° C. under nitrogen. The dark solution was cooled to -50° C. and methyl 4-formylbutyrate (1.5 g) was added dropwise. The pale solution was stirred for 30 minutes at about -60° C., allowed to warm to -10° C., poured on to ice-sodium chloride solution and extracted with ether. The extract was washed with dilute hydrochloric acid, dried and evaporated and the residue was extracted with petroleum spirit to give a mixture of (Z) and (E) esters as an oil (2.8 g). Isomerisation by the method described in (b) above gave the title compound (2.1 g), m.p. 50° C.

Workup

  1. temperatureto warm to -10° C.
  2. extractionextracted with ether
  3. washThe extract was washed with dilute hydrochloric acid
  4. customdried
  5. customevaporated
  6. extractionthe residue was extracted with petroleum spirit
  7. customto give

Sources & evidence

ORD record
ord-e719b458560646918db7ca46961827b3
Source dataset
uspto-grants-1985_04
Patent number
US04513005

Reaction notes

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