Tetrabutylammonium Fluoride → dimethyl 4-[5-((E)-5-ethyl-5-hydroxy-1-methylhept-1-enyl)-2-thienylmethoxy]phthalate

HRID 49322Notes

Reaction equation

[CH2:1]([C:3]([O:32][Si](CC)(CC)CC)([CH2:30][CH3:31])[CH2:4][CH2:5]/[CH:6]=[C:7](/[C:9]1[S:13][C:12]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([C:26]([O:28][CH3:29])=[O:27])[C:19](=[CH:24][CH:25]=2)[C:20]([O:22][CH3:23])=[O:21])=[CH:11][CH:10]=1)\[CH3:8])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([C:3]([OH:32])([CH2:30][CH3:31])[CH2:4][CH2:5]/[CH:6]=[C:7](/[C:9]1[S:13][C:12]([CH2:14][O:15][C:16]2[CH:17]=[C:18]([C:26]([O:28][CH3:29])=[O:27])[C:19](=[CH:24][CH:25]=2)[C:20]([O:22][CH3:23])=[O:21])=[CH:11][CH:10]=1)\[CH3:8])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

750 mg (1.3 mmol) of dimethyl 4-[5-((E)-5-ethyl-1-methyl-5-triethylsilanyloxyhept-1-enyl)-2-thienylmethoxy]phthalate are dissolved in 30 mL of THF. 2.6 mL (2.6 mmol) of a 1.0 M tetrabutylammonium fluoride solution are added and the reaction medium is heated at 60° C. for 3 hours. After treatment with ammonium chloride solution and extraction with ethyl acetate, the organic phases are combined, dried and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica. A yellow oil is obtained (m=355 mg; Y=59%).

Workup

extractionAfter treatment with ammonium chloride solution and extraction with ethyl acetate
customdried
concentrationconcentrated under reduced pressure
customThe residue is purified by chromatography on a column of silica
customA yellow oil is obtained (m=355 mg; Y=59%)

Sources & evidence

ORD record: ord-fb3f364050e142118d2731b5e60994d8
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706725B1

Reaction notes

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