Acetate → HCID 15864470, compound

HRID 1419605Notes

Reaction equation

HRID 1419605 reaction equation
[S:1]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([O:11][C:12](=[O:14])[CH3:13])[CH3:10])(=[O:3])=[O:2].C([O-])(=O)C.S(C1C=CC(C)=CC=1)(OCCCCC(O)C)(=O)=O.COC(C1C=CC=CC=1)(C(F)(F)F)C([O-])=O>>[S:1]([C:15]1[CH:16]=[CH:17][C:18]([CH3:19])=[CH:20][CH:21]=1)([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][C:12](=[O:14])[CH3:13])=[CH2:10])(=[O:2])=[O:3]

Participants

5

Reactant 4

HCID 175AcetateHCID 22174048HCID 22174048, compoundHCID 53961483HCID 53961483, compound2×HCID 54505037HCID 54505037, compound

Product 1

HCID 15864470HCID 15864470, compound

Procedure

1H NMR analysis indicated 5-acetoxyhexyl tosylate as the sole product, and hydrolysis of the acetate, conversion of the resulting 5-hydroxyhexyl tosylate to the α-methoxy-α-trifluoromethylphenylacetate (using the corresponding optically pure acid chloride), 1H NMR analysis and comparison to the racemate indicated 78% ee for 5-acetoxyhexyl tosylate.

Sources & evidence

ORD record
ord-6e984ae818d747b184f74fbab18aa8ca
Source dataset
uspto-grants-1999_03
Patent number
US05886214

Reaction notes

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