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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1417633Generated: October 31, 2026

Trifluoroacetic acid → (6aR,7S,9aS,11S,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-3-oxo-5-diphenoxyphosphinyloxy-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

https://huagongshe.com/reaction/1417633

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantAnisoleHCID 7519—
Reactant(6aR,7S,9aS,11S,13aS)-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a, 10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-3-oxo-5-diphenoxyphosphinyloxy-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleHCID 86753840—
SolventDichloromethaneHCID 6344—
Product(6aR,7S,9aS,11S,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7,10,10-tetramethyl-3-oxo-5-diphenoxyphosphinyloxy-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleHCID 8675384191.3%

Reaction Steps

To a solution of the above Compound (56a) (256 mg, 0.36 mmol) in 2.5 ml of dry dichloromethane were added 50 μl of anisole and 2.5 ml of trifluoroacetic acid, and the mixture stirred for 10 min at the same temperature, and then for one hour at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was made basic with 7% aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a column chromatography (silica gel 15 g; ethyl acetate) to give 203 mg (91%) of Compound (57a).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05876984
Source datasetuspto-grants-1999_03
ORD IDord-f645afbcbad640f4908ac8934868dc0f
Source noteuspto-grants-1999_03