Sodium Sulfate → HCID 86736668, compound

HRID 224260Notes

Reaction equation

[F:1]/[C:2](=[C:8](/[CH3:22])\[CH:9]=[CH:10]\[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([O:18][CH3:19])=[C:13]([CH3:20])[C:12]=1[Cl:21])/[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>>[F:1]/[C:2](/[C:8](/[CH3:22])=[CH:9]/[CH2:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([O:18][CH3:19])=[C:13]([CH3:20])[C:12]=1[Cl:21])=[CH:3]\[OH:4]

Participants

Reactant 3

HCID 24436Sodium Sulfate

HCID 12788547HCID 12788547, compound

HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 86736668HCID 86736668, compoundYield 80%

Conditions

Temperature: -45 °C

Procedure

A solution of 8.5 g. (24.5 mmol) of ethyl 2Z,4E-2-fluoro-3-methyl-5-(2,6-dichloro-3-methyl-4-methoxyphenyl)pentadienoate was stirred under argon and cooled to -45° C. Diisobutylaluminum hydride (DIBAH) was added slowly until three equivalents had been added and no starting material remained by tlc. Saturated aqueous sodium sulfate (5 ml.) was added at -10° C. and the mixture was allowed to warm to 30° C. for completion of hydrolysis. The mixture was filtered through Celite and the filtrate was evaporated. The residue was chromatographed on silica to give 6.0 g. (80% yield) of 2Z,4E-2-fluoro-3-methyl-5-(2,6-dichloro-3-methyl-4-methoxyphenyl)pentadien-1-ol.

Workup

additionhad been added
temperatureto warm to 30° C. for completion of hydrolysis
filtrationThe mixture was filtered through Celite
customthe filtrate was evaporated
customThe residue was chromatographed on silica
customto give 6.0 g

Sources & evidence

ORD record: ord-c485c78617b847a7a2976e5baa797c93
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04231944

Reaction notes

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