Aluminium lithium hydride → 1-(2-Fluoro-3-hydroxyprop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropane

HRID 963814Notes

Reaction equation

HRID 963814 reaction equation
[F:1][C:2]([C:16](OC)=[O:17])=[CH:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]3[O:13][CH2:14][O:15][C:9]=3[CH:8]=2)[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[F:1][C:2]([CH2:16][OH:17])=[CH:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]3[O:13][CH2:14][O:15][C:9]=3[CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 538090221-(2-Fluoro-2-(methoxycarbonyl)ethenyl)-1-(3,4-methylenedioxyphenyl)cyclopropane

Product 1

HCID 541098611-(2-Fluoro-3-hydroxyprop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropaneYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The method of Example 9 was repeated using 1-(2-Fluoro-2-(methoxy-carbonyl)ethenyl)-1-(3,4-methylene-dioxyphenyl)cyclopropane (Example 6) (0.98 g), diethyl ether (15 ml) and lithium aluminium hydride (0.37 g) to yield the title compound (0.78 g, 88%).

Sources & evidence

ORD record
ord-915fca8f9872402c8dfc5b359b151919
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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