Dimethylformamide → HCID 12788561, compound

HRID 224257Notes

Reaction equation

[CH3:1]/[C:2](/[CH:6]=[CH:7]/[C:8](/[F:21])=[C:9](\[CH3:20])/[CH:10]=[CH:11]/[C:12]1[C:16]([CH3:17])=[C:15]([CH3:18])[S:14][C:13]=1[CH3:19])=[CH:3]\[CH2:4][OH:5].O1CCC[CH2:23]1.[H-].[Na+].CN(C)C=O>O>[CH3:1]/[C:2](/[CH:6]=[CH:7]/[C:8](/[F:21])=[C:9](\[CH3:20])/[CH:10]=[CH:11]/[C:12]1[C:16]([CH3:17])=[C:15]([CH3:18])[S:14][C:13]=1[CH3:19])=[CH:3]\[CH2:4][O:5][CH3:23]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 0.400 g. (1.31 mmole) of 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-2,4,6,8-nonatetraen-1-ol in 5 ml. of tetrahydrofuran was added to a suspension of 0.11 g. (2.6 mmole) of a 56% sodium hydride dispersion in a mixture of 10 ml. of dry tetrahydrofuran and 20 ml. of dry dimethylformamide. This reaction mixture was stirred at 23° C. for 14 hours, poured into water and extracted with ether-hexane (1:1 parts by volume). The extracts were washed with water, dried with magnesium sulfate, filtered and evaporated to give an orange product which was crystallized from ether-hexane (1:4 parts by volume) to give 220 mg. (52% yield) of 2E,4E,6Z,8E-3,7-dimethyl-6-fluoro-9-(2,4,5-trimethyl-3-thienyl)-1-methoxy-2,4,6,8-nonatetraene as a light orange solid, m.p. 117°-118° C.

Workup

extractionextracted with ether-hexane (1:1 parts by volume)
washThe extracts were washed with water
dry with materialdried with magnesium sulfate
filtrationfiltered
customevaporated
customto give an orange product which
customwas crystallized from ether-hexane (1:4 parts by volume)
customto give 220 mg

Sources & evidence

ORD record: ord-91d209cbaa214391b7d273eeac5f71fc
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04231944

Reaction notes

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