Hexane → 3-Decynoic acid

HRID 1722347Notes

Reaction equation

HRID 1722347 reaction equation
[C:1]([OH:6])(=[O:5])[CH2:2][C:3]#[CH:4].C([Li])CCC.[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].ICCCCCC>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[C:1]([OH:6])(=[O:5])[CH2:2][C:3]#[C:4][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 8058HexaneHCID 125271-IodohexaneHCID 1375473-Butynoic AcidHCID 178418339Butyllithium

Product 1

HCID 5493723-Decynoic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

To 6.8g (70 mmol) of 3-butynoic acid dissolved in 150ml of 1:1 tetrahydrofuran (THF):hexamethyl phosphoric triamide (HMPA) and cooled to -20°C. is added via syringe a solution of n-butyl lithium in hexane (1.6N, 2 equiv). The mixture was allowed to warm to 0°C. The mixture is stirred for 30 minutes at this temperature and then 150g (1.1 equiv) of 1-iodohexane is added dropwise as a solution in 20ml of THF. The mixture is allowed to warm to room temperature and then is partitioned between ether and water. The aqueous layer is acidified with 3N H2SO4 and extracted with ether. The combined organic extracts are washed with brine and dried (Na2SO4). Evaporation of the volatiles in vacuo and chromatography of the crude on silica gel (ethyl acetate/hexane/acetic acid; 10:90:0.1) affords 4.5g of pure 3-decynoic acid.

Workup

  1. temperatureto warm to room temperature
  2. customis partitioned between ether and water
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the volatiles in vacuo and chromatography of the crude on silica gel (ethyl acetate/hexane/acetic acid; 10:90:0.1)

Sources & evidence

ORD record
ord-7096c1ba22334a5f934b6d735bcc96a9
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

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