Sodium Chloride → 2,3-Epoxypropoxy-2-(5-methyl-1,3,4-oxadiazol-2-yl)-benzene

HRID 223356Notes

Reaction equation

HRID 223356 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:6][N:5]=1.[CH2:16]([CH:18]1[O:20][CH2:19]1)Br.[Cl-].[Na+]>O1CCCC1.CN(P(N(C)C)(N(C)C)=O)C>[O:20]1[CH2:19][CH:18]1[CH2:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[O:8][C:4]([CH3:3])=[N:5][N:6]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 135979760ortho-(5-Methyl-1,3,4-oxadiazol-2-yl)-phenol

Product 1

HCID 129617442,3-Epoxypropoxy-2-(5-methyl-1,3,4-oxadiazol-2-yl)-benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

1.6 g of sodium hydride, in the form of a 55% strength suspension in paraffin oil (0.036 mole) are introduced into 70 ml of anhydrous tetrahydrofuran and 6.3 g (0.036 mole) of ortho-(5-methyl-1,3,4-oxadiazol-2-yl)-phenol, dissolved in 50 ml of tetrahydrofuran, are added dropwise. 5 g (0.036 mole) of epibromohydrin are then introduced dropwise, 10 ml of hexamethylphosphorotriamide are added to the reaction mixture, and the whole is stirred for 32 hours at room temperature. Thereafter, the reaction mixture is poured into 500 ml of aqueous sodium chloride solution and repeatedly extracted by shaking with diethyl ether. The combined ether extracts are dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to give a yellow oil. This crystallizes on triturating with a toluene/hexane mixture. 5.5 g (66% of theory) of colorless crystals are obtained; melting point 38°-40° C.

Workup

  1. additionare added dropwise
  2. extractionrepeatedly extracted
  3. stirringby shaking with diethyl ether
  4. dry with materialThe combined ether extracts are dried over anhydrous sodium sulfate
  5. concentrationconcentrated on a rotary evaporator
  6. customto give a yellow oil
  7. customThis crystallizes
  8. customon triturating with a toluene/hexane mixture
  9. custom5.5 g (66% of theory) of colorless crystals are obtained

Sources & evidence

ORD record
ord-0ab34f2942c14f70b236df0ff8d51401
Source dataset
uspto-grants-1982_10
Patent number
US04353904

Reaction notes

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