Triethylamine → HCID 57776962, compound

HRID 660967Notes

Reaction equation

HRID 660967 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]1[O:13][CH:12]1[CH2:14][OH:15].C(N(CC)CC)C>O1CCCC1>[C:2](=[O:3])([O:15][CH2:14][CH:12]1[O:13][CH2:11]1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11164GlycidolHCID 15891Phenyl chloroformate

Product 1

HCID 57776962HCID 57776962, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A three-necked round bottom flask, equipped with a reflux condenser, an addition funnel, and a nitrogen gas inlet is charged with 25.00 g (0.160 mole) of phenyl chloroformate and 70 g of THF. The reactor was placed in a 0° C. bath and purged with nitrogen. After 30 minutes, a solution of 13.00 g (0.175 mole) glycidol, 19.50 g (0.193 mole) triethylamine, and 75 g of anhydrous tetrahydrofuran (THF) was added drop wise over the course of one hour, after which the reaction was allowed to warm to room temperature and allowed to stir overnight under a nitrogen atmosphere. The contents of the reactor were discharged, filtered, and evaporated to dryness to afford 29.51 g of crude product, which was purified by flash chromatography using silica gel and eluted with a 1:1 solution of iso-propyl acetate and hexane. See FIG. 10.

Workup

  1. customA three-necked round bottom flask, equipped with a reflux condenser, an addition funnel, and a nitrogen gas inlet
  2. customwas placed in a 0° C.
  3. custompurged with nitrogen
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-64f3ab0a1f224d2eb4bae1fc8b3a818d
Source dataset
uspto-grants-2011_12
Patent number
US08084553B2

Reaction notes

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