Aluminium lithium hydride → 1-(4-Difluoromethoxyphenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl)cyclopropane

HRID 963816Notes

Reaction equation

HRID 963816 reaction equation
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:13]=[C:14]([F:19])[C:15](OC)=[O:16])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[F:20][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH:13]=[C:14]([F:19])[CH2:15][OH:16])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 539014161-(4-Difluoromethoxyphenyl)-1-(2-fluoro-2(methoxycarbonyl)ethenyl)cyclopropane

Product 1

HCID 541079581-(4-Difluoromethoxyphenyl)-1-(2-fluoro-3-hydroxyprop-1-enyl)cyclopropaneYield 90.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The method of Example 9 was repeated using 1-(4-difluoromethoxyphenyl)-1-(2-fluoro-2(methoxycarbonyl)-ethenyl)cyclopropane (Example 8) (0.77 g), diethyl ether (10 ml) and lithium aluminium hydride (0.2 g) to yield the title compound (0.63 g, 89%).

Sources & evidence

ORD record
ord-0a216a194cb94b9e97207e7802dfd30b
Source dataset
uspto-grants-1998_06
Patent number
US05763700

Reaction notes

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