Trifluoroacetic acid → Methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

HRID 5882Notes

Reaction equation

HRID 5882 reaction equation
[CH:1]1([C:7]2[C:16]([NH:17][C:18](=[O:20])[CH3:19])=[C:15]([Cl:21])[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]=2[OH:22])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.FC(F)(F)C(O)=O>>[C:18]([NH:17][C:16]1[C:7]2[CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]3[O:22][C:8]=2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][C:15]=1[Cl:21])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19794428Methyl 3-(3-Cyclohexenyl)-4-Acetylamino-5-Chlorosalicylate

Product 1

HCID 15136047Methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate

Procedure

A mixture of 1.2 g of methyl 3-(3-cyclohexenyl)-4-acetylamino-5-chlorosalicylate and 5 ml trifluoroacetic acid are stirred at room temperature overnight. The acid is removed under vacuum and the residue diluted with ether, washed with sodium bicarbonate, then water, dried and evaporated to dryness to give crude methyl 1-acetylamino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylate. This product is purified by flash chromatography using 10% ethyl acetate/hexane to give pure product.

Workup

  1. customThe acid is removed under vacuum
  2. additionthe residue diluted with ether
  3. washwashed with sodium bicarbonate
  4. dry with materialwater, dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-59cc86bc4e3c4b42bb0e0e6a3f0c01e9
Source dataset
uspto-grants-1993_09
Patent number
US05246942

Reaction notes

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