Sulfuric acid magnesium salt (1:1) → HCID 12788559, compound

HRID 224256Notes

Reaction equation

[CH3:1]/[C:2](/[CH:8]=[CH:9]/[C:10](/[F:23])=[C:11](\[CH3:22])/[CH:12]=[CH:13]/[C:14]1[C:18]([CH3:19])=[C:17]([CH3:20])[S:16][C:15]=1[CH3:21])=[CH:3]\[C:4](OC)=[O:5].[H-].C([Al+]CC(C)C)C(C)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH3:1]/[C:2](/[CH:8]=[CH:9]/[C:10](/[F:23])=[C:11](\[CH3:22])/[CH:12]=[CH:13]/[C:14]1[C:18]([CH3:19])=[C:17]([CH3:20])[S:16][C:15]=1[CH3:21])=[CH:3]\[CH2:4][OH:5]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 1.05 g. (31.4 mmole) of methyl 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraenoate in 100 ml. of methylene chloride was cooled to -60° C. under argon and 5.2 ml. (69 mmole) of diisobutylaluminium hydride were added dropwise thereto. The temperature was raised to -10° C. for 10 minutes and 4 ml. of a saturated solution of magnesium sulfate were added thereto. This mixture was stirred at 25° C. for 2 hours, filtered through celite and evaporated to give a light yellow solid which was crystallized from hexane-ether (4:1 parts by volume) to give 700 mg. (73% yield) of 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraen-1-ol, m.p. 106°-107.5° C.

Workup

filtrationfiltered through celite
customevaporated
customto give a light yellow solid which
customwas crystallized from hexane-ether (4:1 parts by volume)
customto give 700 mg

Sources & evidence

ORD record: ord-1b746c9591194950ac831db7f9cfb59c
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04231944

Reaction notes

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