Sodium Sulfate → HCID 12960834, compound

HRID 1156440Notes

Reaction equation

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

Participants

Conditions

Temperature: -45 °C

Procedure

A solution of 6.5 g. (23 mmol) of ethyl (2E,4E)-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-thienyl)-2,4-pentadienoate in diethyl ether was stirred under argon and cooled to -45° C. Diisobutylaluminum hydride (DIBAH) was added slowly until three equivalents had been added and no starting ester remained. Five ml. of a saturated solution of sodium sulfate was added at -10° C. and the mixture was allowed to come to 30° C. Filtration through Celite and subsequent washing of the residue with methylene chloride gave a clear yellow solution of 2E,4E-2-fluoro-3-methyl-5-(2,4,5-trimethyl-3-thienyl)-2,4-pentadien-1-ol which was carried on to the next step without further purification.

Workup

additionhad been added
customto come to 30° C
filtrationFiltration through Celite
washsubsequent washing of the residue with methylene chloride

Sources & evidence

ORD record: ord-73f8871e3c7b4310809206e4108b9564
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04335248

Reaction notes

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