Tetrahydrofuran → (E)-3-(7-(4-fluorophenyl)-9,9-dimethyl-1,4-dioxaspiro-{4,5}dec-7-en-8-yl)propenal

HRID 654543Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][C:10]3([CH2:15][C:16]([CH3:21])([CH3:20])[C:17]=2C=O)[O:14][CH2:13][CH2:12][O:11]3)=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.C(=NC1CCCCC1)C.[CH2:39]1C[O:42][CH2:41][CH2:40]1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][C:10]3([CH2:15][C:16]([CH3:20])([CH3:21])[C:17]=2/[CH:39]=[CH:40]/[CH:41]=[O:42])[O:14][CH2:13][CH2:12][O:11]3)=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 2724682Lithium diisopropylamide

HCID 10964544N-cyclohexylethanimine

HCID 150569627-(4-Fluorophenyl)-9,9-dimethyl-1,4-dioxaspiro{4,5}-dec-7-en-8-carboxaldehyde

Product 1

HCID 15056963(E)-3-(7-(4-fluorophenyl)-9,9-dimethyl-1,4-dioxaspiro-{4,5}dec-7-en-8-yl)propenal

Procedure

In a manner similar to Scheme I, 26 (2.08 g, 7.17 mmol) was treated with the LDA-derived anion of ethylidenecyclohexylamine (1.36 g, 10.8 mmol) in anhydrous THF at 0°-5° C. and after workup and purification by SiO2 using 6:1 hexanes:EtOAc as eluent provided 1.25 g of orange solid.

Workup

customat 0°-5° C.
customafter workup and purification by SiO2 using 6:1 hexanes

Sources & evidence

ORD record: ord-60eb72126d984c0193f424c64c64853a
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05132312

Reaction notes

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