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

HRID 2112739Notes

Reaction equation

HRID 2112739 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]>C1COCC1>[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 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 2-methyl-1,3-benzoxazol-6-ol (7.1 g, 48.7 mmol) in THF (150 mL) was cooled to 10° C. and triethylamine (11.3 mL, 81.3 mmol) was added in one portion, followed by the addition of acetyl chloride (5.8 mL, 81.3 mmol) in small portions. After addition was completed the reaction mixture was stirred at room temperature over night, partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give sub-title compound (8.2 g).

Workup

  1. additionAfter addition
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7985e78965b041ca9b3af9c38145e4bc
Source dataset
uspto-grants-2009_04
Patent number
US07524856B2

Reaction notes

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