Glycidol → HCID 21391891, compound

HRID 462001Notes

Reaction equation

HRID 462001 reaction equation
[H-].[Na+].[CH2:3]1[O:5][CH:4]1[CH2:6][OH:7].C(S([C:13]1[S:14][C:15]([C:18]([NH:20][CH2:21][CH2:22][C:23]23[CH2:32][CH:27]4[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]4)[CH2:24]2)[CH2:30]3)=[O:19])=[CH:16][N:17]=1)(=O)=O)C>O1CCCC1>[O:5]1[CH:4]([CH2:6][O:7][C:13]2[S:14][C:15]([C:18]([NH:20][CH2:21][CH2:22][C:23]34[CH2:32][CH:27]5[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]5)[CH2:24]3)[CH2:30]4)=[O:19])=[CH:16][N:17]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 11164GlycidolHCID 24758Sodium hydrideHCID 21391889HCID 21391889, compound

Product 1

HCID 21391891HCID 21391891, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

In this preparation 0.0525 mole of sodium hydride in a 50% mineral oil mixture is stirred in 300 ml. of anhydrous tetrahydrofuran, under nitrogen, then cooled to -30° C and 0.055 mole of glycidol is added dropwise. The mixture is allowed to warm to -5° C and stirred for ten minutes and then recooled to -30° C. A solution of 0.05 mole of 2-ethylsulfonyl-5-[2-(adamant-1-yl)ethylaminocarbonyl]thiazole in 100 ml. of anhydrous tetrahydrofuran is added dropwise and the resulting mixture allowed to warm to 0° C. Additional solvent is added as needed to facilitate stirring. The mixture is maintained at 30 minutes at 0° C and then poured into 500 ml. of ethyl acetate, extracted with 100 ml. of water, and then with 100 ml. of aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under vacuum affording an oily residue which is then further purified by chromatography on silica gel eluting with 40% ethyl acetate-60% hexane, by vol., affording 1,2-epoxy-3-[5-(2-[adamant-1-yl]ethylaminocarbonyl)thiazol-2-yloxy]propane.

Workup

  1. stirringstirred for ten minutes
  2. customrecooled to -30° C
  3. temperatureto warm to 0° C
  4. additionAdditional solvent is added
  5. stirringto facilitate stirring
  6. temperatureThe mixture is maintained at 30 minutes at 0° C
  7. additionpoured into 500 ml
  8. extractionof ethyl acetate, extracted with 100 ml
  9. dry with materialof aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate is evaporated under vacuum
  12. customaffording an oily residue which
  13. customis then further purified by chromatography on silica gel eluting with 40% ethyl acetate-60% hexane, by vol.

Sources & evidence

ORD record
ord-94a1f74352c4462f94db9f4ad0cd9cae
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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