Acetyl chloride → 2-Methylbenzo[d]oxazol-6-yl acetate

HRID 270086Notes

Reaction equation

HRID 270086 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>O1CCCC1>[C:19]([O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[O:3][C:4]=2[CH:10]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 6765042-Methyl-1,3-benzoxazol-6-ol

Product 1

HCID 156622632-Methylbenzo[d]oxazol-6-yl acetateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 2-methyl-1,3-benzoxazol-6-ol (7.1 g, 47.8 mmol) in tetrahydrofuran was cooled to 10° C. and triethylamine (5.8 mL, 81.3 mmol) was added in one portion, followed by the addition of acetyl chloride (11.3 mL, 81.6 mmol) in small portions. After stirring at room temperature over night the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed twice with water and concentrated to give the titled compound (8.2 g, 90%) as a beige solid.

Workup

  1. customwas partitioned between water and ethyl acetate
  2. washThe organic phase was washed twice with water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b5137d93f7e74bada7eb5d0b17c0468b
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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