Trifluoroacetic acid → 3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

HRID 20699Notes

Reaction equation

HRID 20699 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][CH2:16][CH2:17][CH:18]([C:24](=[O:45])[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:26]=1OC1CCCC1)[C:19]([O:21]CC)=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[CH2:8]([O:15][CH2:16][CH2:17][C:18]1[C:19](=[O:20])[O:21][C:26]2[C:25]([C:24]=1[OH:45])=[CH:30][CH:29]=[C:28]([O:31][CH3:32])[C:27]=2[O:33][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68741697Ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate

Product 1

HCID 866181373-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (35 mL) was added dropwise to a solution of ethyl 4-(benzyloxy)-2-(2,3-bis(cyclopentyloxy)-4-methoxybenzoyl)butanoate (14 g, 25 mmol) and dichloromethane (280 mL) at rt. The reaction was maintained overnight, diluted with dichloromethane (200 mL), and washed with sat'd NaHCO3 (200 mL×2) and then brine (200 mL). The organic layer was dried, filtered, concentrated, and purified by silica gel chromatography (ethyl acetate:petroleum ether) to give 3-(2-(benzyloxy)ethyl)-8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one: MS (ESI): 411.

Workup

  1. temperatureThe reaction was maintained overnight
  2. washwashed with sat'd NaHCO3 (200 mL×2)
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (ethyl acetate:petroleum ether)

Sources & evidence

ORD record
ord-3142ede221b143209de518affd1fa55e
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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