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

HRID 1276175Notes

Reaction equation

HRID 1276175 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 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-f05afbec90454e15a93f789a6f12d44d
Source dataset
uspto-grants-2000_12
Patent number
US06166011

Reaction notes

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