Trifluoroacetic acid → HCID 19363419, compound

HRID 850496Notes

Reaction equation

HRID 850496 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH:25](O)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:33][CH3:34])[C:23]=3[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:18]2=[O:35])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:33][CH3:34])[C:23]=3[O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:18]2=[O:35])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 19363238HCID 19363238, compound

Product 1

HCID 19363419HCID 19363419, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-(4-Benzyloxyphenyl)ethyl]-3-hydroxy-5-methoxy-4pentyloxy-2,3-dihydroisoindol-1-one (142 mg, 0.30 mmol, 1.0 eq) was dissolved in dichloromethane (3 ml), and triethylsilane (0.095 ml, 0.60 mmol, 2.0 eq) was added. The mixture was stirred for 10 minutes at room temperature. Trifluoroacetic acid was added thereto, and the mixture was further stirred for 4 hours. A saturated aqueous sodium hydrogencarbonate solution (30 ml) was added to this reaction mixture. The mire was extracted twice with ethyl acetate (30 ml). The organic layers were combined, then washed with saturated brine (60 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give 2-[2-(4-benzyloxyphenyl)ethyl]-5-methoxy-4-pentyloxy-2,3-dihydroisoindol-1-one (136 mg, 99.8%) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred for 4 hours
  2. extractionThe mire was extracted twice with ethyl acetate (30 ml)
  3. washwashed with saturated brine (60 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9023a1e15ffc49dd81cd9de6504b228f
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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