1-Octyne → HCID 13588520, compound

HRID 1284439Notes

Reaction equation

HRID 1284439 reaction equation
O1CC[CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][CH2:22]CCCCC.[CH:29]#CCCCCCC.C([Li])CCC.C(Br)CCCCCO>O1CCCC1.CCCCCC.CN(C)P(=O)(N(C)C)N(C)C.O>[C:8]([O:7][CH:2]([CH2:3][CH3:4])[CH3:29])(=[O:9])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

10

Reactant 5

HCID 123701-OctyneHCID 779706-Bromo-1-hexanolHCID 263182Tetrahydropyranyl ether2×HCID 35630467-tetradecyn-1-olHCID 178418339Butyllithium

Product 1

HCID 13588520HCID 13588520, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

Tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol. To a cooled solution (-15° C.) of 1-octyne (7.95 g) in 30 ml of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise 30.4 ml of 2.09M butyllithium in hexane. The addition took 30 minutes, after which the reaction was warmed to 0° C. and then cooled to -10° C. This solution was added slowly to a cold (0° C.) solution of the tetrahydropyranyl ether derivative of hexamethylene bromohydrin (14.80 g) in 50 ml of hexamethylphosphoric triamide under nitrogen. The reaction mixture was allowed to warm to room temperature, stirred overnight, poured into cold water, and extracted three times with hexane. The combined organic layers were washed with water (three times) and brine, and dried with anhydrous Na2SO4. Removal of solvent under reduced pressure yielded 18.55 g of impure tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol as a yellow oil. This material was used without further purification in the next step.

Workup

  1. additionThe addition
  2. temperaturecooled to -10° C
  3. temperatureto warm to room temperature
  4. extractionextracted three times with hexane
  5. washThe combined organic layers were washed with water (three times) and brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-67481f5b33984f97a48a7964aecd40c6
Source dataset
uspto-grants-1986_01
Patent number
US04563348

Reaction notes

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