Acetic Anhydride → 2-Chloro-1,3-benzoxazol-6-yl acetate

HRID 2119403Notes

Reaction equation

HRID 2119403 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>ClCCl>[C:19]([O:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([Cl:8])[O:10][C:11]=2[CH:17]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 234412462-Chloro-1,3-benzoxazol-6-OL

Product 1

HCID 183401792-Chloro-1,3-benzoxazol-6-yl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.48 ml) was added to a suspension of 2-chloro-1,3-benzoxazol-6-ol (1.63 g) [see Preparation 34] in dichloromethane (20 ml), and after 5 minutes acetic anhydride (1.01 ml) was added. The reaction mixture was stirred at room temperature for 18 hours, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0, changing to 40:10, changing to 0:100, by volume, hexane:ethyl acetate to afford 2-chloro-1,3-benzoxazol-6-yl acetate (1.63 g) as an oil.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 100:0

Sources & evidence

ORD record
ord-c361fdc600bb4971b410e8f5271dbd1d
Source dataset
uspto-grants-2004_02
Patent number
US06686357B1

Reaction notes

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