Trifluoroacetic acid → HCID 68847088, compound

HRID 2378508Notes

Reaction equation

HRID 2378508 reaction equation
[OH:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2.[CH:19]([O:21][CH:22]=[CH2:23])=[CH2:20].F[C:25](F)(F)[C:26](O)=O>C1COCC1.CCCCC.CCOC(C)=O>[CH2:19]([O:21][CH:22]([O:1][C:2]12[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH3:23])[CH2:20][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8024Vinyl etherHCID 67491946HCID 67491946, compound

Product 1

HCID 68847088HCID 68847088, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22335286Ethyl acetate pentaneSolvent

Procedure

A mixture of 2 g (7.9 mmol) of (16) and 0.84 ml (8.7 mmol) buthyl vinyl ether in 2 ml THF was stirred at room temperature in the presence of 20 μl (0.32 mmol) trifluoroacetic acid for 1 day. Flash chromatography of the reaction mixture, using SiO2 (80 g) and pentane/EtOAc=9:1 as eluent, afforded 2.3 g (82%) of (27) as a ˜1:1 mixture of diastereomers.

Sources & evidence

ORD record
ord-75193053543243fd9ea8d3c3ab49d7dd
Source dataset
uspto-grants-2008_12
Patent number
US07470820B2

Reaction notes

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