Hexane → 8-Hydroxy-9-(4-pentoxyphenoxy)-5-nonynoic acid

HRID 1165257Notes

Reaction equation

HRID 1165257 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[Li]CCCC.CCCCCC.[CH2:20]([O:25][C:26]1[CH:36]=[CH:35][C:29]([O:30][CH2:31][CH:32]2[CH2:34][O:33]2)=[CH:28][CH:27]=1)[CH2:21][CH2:22][CH2:23][CH3:24]>CN(P(N(C)C)(N(C)C)=O)C.O>[OH:33][CH:32]([CH2:31][O:30][C:29]1[CH:28]=[CH:27][C:26]([O:25][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:36][CH:35]=1)[CH2:34][C:6]#[C:5][CH2:4][CH2:3][CH2:2][C:1]([OH:8])=[O:7]

Participants

7

Reactant 4

HCID 8058HexaneHCID 1430365-Hexynoic acidHCID 147482762-(4-Pentoxyphenoxymethyl)oxiraneHCID 178418339Butyllithium

Product 1

HCID 147482778-Hydroxy-9-(4-pentoxyphenoxy)-5-nonynoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent2×

Procedure

A dry flask equipped with an addition funnel and a mechanical stirrer under Ar was charged with 100 ml of HMPA and 9.7 g of 5-hexynoic acid. The flask was cooled in an ice water bath and a solution of n-BuLi in hexane (118 ml, 0.189 mole) was added dropwise. The resulting reaction mixture was stirred for 1.5 hr and then a solution of 24.5 g of 2-(4-pentoxyphenoxymethyl)oxirane, the product of Example 14a, in 20 ml of HMPA was added and stirring was continued for 2 days. The reaction mixture was poured into water and extracted with Et2O three times. The ether solution was washed with aqueous NH4OH twice. The aqueous solution was acidified with HCl and extracted with Et2O. The ether solution was washed with saturated NaCl solution, dried over MgSO4. Solvent was removed to give the crude product which was recrystallized in cyclohexane to give the title compound, mp 58.0°-60.0°.

Workup

  1. customA dry flask equipped with an addition funnel and a mechanical stirrer under Ar
  2. temperatureThe flask was cooled in an ice water bath
  3. customThe resulting reaction mixture
  4. stirringstirring
  5. waitwas continued for 2 days
  6. extractionextracted with Et2O three times
  7. washThe ether solution was washed with aqueous NH4OH twice
  8. extractionextracted with Et2O
  9. washThe ether solution was washed with saturated NaCl solution
  10. dry with materialdried over MgSO4
  11. customSolvent was removed
  12. customto give the crude product which
  13. customwas recrystallized in cyclohexane

Sources & evidence

ORD record
ord-f76a9d46397c4201b5f1554565528a6e
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Reaction notes

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