Ethylene Oxide → HCID 20062817, compound

HRID 2166154Notes

Reaction equation

HRID 2166154 reaction equation
C([Li])CCC.[CH2:6]([O:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]#[CH:8].B(F)(F)F.[CH3:22][CH2:23][O:24]CC.O1CC1.[Cl-].[NH4+]>C1COCC1>[C:12]1([CH2:11][CH2:10][O:9][CH2:6][C:7]#[C:8][CH2:22][CH2:23][OH:24])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 25517Ammonium ChlorideHCID 12407536{2-[(Prop-2-yn-1-yl)oxy]ethyl}benzeneHCID 178418339Butyllithium

Product 1

HCID 20062817HCID 20062817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (1.6M in hexane, 35 ml) was added to a stirred solution of the product of step (i) (8.0 g) in dry THF (50 ml) at -78° under nitrogen. Boron trifluoride etherate (6.8 ml) was added and the mixture was stirred at -78° for 30 min. Oxirane (7 ml) was added and the mixture was stirred at -78° for 1 h, treated with saturated saturated aqueous ammonium chloride (100 ml), allowed to warm to room temperature, and extracted with ER (2×100 ml). The organic extracts were washed with water and brine, dried and concentrated to an orange oil which was purified by FCC eluting with H-ER (2:1) to give the title compound as a pale yellow oil (3.95 g). T.l.c. (H-ER 2:1) Rf 0.10.

Workup

  1. stirringthe mixture was stirred at -78° for 1 h
  2. extractionextracted with ER (2×100 ml)
  3. washThe organic extracts were washed with water and brine
  4. customdried
  5. concentrationconcentrated to an orange oil which
  6. customwas purified by FCC
  7. washeluting with H-ER (2:1)

Sources & evidence

ORD record
ord-9bcad3f079594ccf904484359745e525
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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