Propargyl alcohol → [3-(2-Chlorophenyl)-1,2-oxazol-5-yl]methanol

HRID 2407657Notes

Reaction equation

HRID 2407657 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](Cl)=[N:16][OH:17].[CH2:19]([OH:22])[C:20]#[CH:21]>C(OCC)C>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:21]=[C:20]([CH2:19][OH:22])[O:17][N:16]=1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 380973329568-74-9

Product 1

HCID 1471845[3-(2-Chlorophenyl)-1,2-oxazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of triethylamine (48 mL) in diethyl ether (0.5 L) was added over two hours to a 0° C. solution of the compound prepared in Example 5 (50.0 g) and propargyl alcohol (31 mL) in diethyl ether (1.2 L). The reaction was stirred at room temperature overnight, washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain the title compound (50.0 g) having the following physical data.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c57dba5bcf7c45099b8755f5405620f7
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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