Propargyl alcohol → HCID 22672768, compound

HRID 1886247Notes

Reaction equation

[CH2:1]([OH:4])[C:2]#[CH:3].C([Li])CCC.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]([CH2:20][CH2:21][CH2:22][CH3:23])[CH3:19])=[O:17].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH2:20]([N:18]([CH3:19])[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:3]#[C:2][CH2:1][OH:4])[CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 1.77 ml of propargyl alcohol, 30 ml of tetrahydrofuran and 7.5 ml of hexamethyl phosphotriamide cooled to -60° C. was admixed with 37.5 ml of a 1.6M solution of butyllithium in hexane and after stirring for 45 minutes at -30° C., 7 g of the product of Step A in solution in 7 ml of tetrahydrofuran were added. The mixture was stirred for 16 hours at ambient temperature and then poured into a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic phase was washed with 2N hydrochloric acid and with a saturated solution of sodium bicarbonate, dried and evaporated to dryness. The 5.78 g of residue were chromatographed on silica (eluant: methylene chloride-ethyl acetate 70-30, then methylene chloride-isopropanol 95-5) to obtain 1.65 g of the desired product.

Workup

stirringThe mixture was stirred for 16 hours at ambient temperature
extractionextracted with ethyl acetate
washThe organic phase was washed with 2N hydrochloric acid and with a saturated solution of sodium bicarbonate
customdried
customevaporated to dryness
customThe 5.78 g of residue were chromatographed on silica (eluant

Sources & evidence

ORD record: ord-405ed342f4db4c179af28bd103931cc2
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05149696

Reaction notes

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