Water → HCID 19986066, compound

HRID 974695Notes

Reaction equation

HRID 974695 reaction equation
C([Li])CCC.[CH2:6]([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:7]#[CH:8].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].O>CCCCCC.O1CCCC1>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:9][CH2:6][C:7]#[C:8][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 82131-BromohexadecaneHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 19986066HCID 19986066, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

50 ml of a 15% by weight solution of butyllithium in hexane was added dropwise at -50° C. to a solution of 11.48 g of 2-tetrahydropyranyl propargyl ether in 220 ml of tetrahydrofuran followed by 25 g of palmityl bromide, and the mixture was stirred for 30 minutes, during which time the temperature of the mixture was allowed to rise to room temperature. The reaction mixture was heated under reflux for 16 hours, poured into water and then extracted twice with diethyl ether. The combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 500 g of silica gel. 14.59 g of the title compound were isolated as an oil from the fractions eluted with a 3:100 by volume mixture of diethyl ether and hexane.

Workup

  1. customto rise to room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 16 hours
  4. extractionextracted twice with diethyl ether
  5. washThe combined extracts were washed with water
  6. customdried
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1078382f1e934edcad69a2f9f72b68f5
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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