1,4-Dioxaspiro[4.5]decan-8-one → 8-(2,2,3,3-Tetrafluoro-2,3-dihydrobenzofuran-7-ylmethylene)-1,4-dioxaspiro[4.5]decane

HRID 1735309Notes

Reaction equation

HRID 1735309 reaction equation
[Br-].[F:2][C:3]1([F:34])[C:7]([F:9])([F:8])[C:6]2[CH:10]=[CH:11][CH:12]=[C:13]([CH2:14][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:5]=2[O:4]1.C([Li])CCC.[CH2:40]1[O:50][C:43]2([CH2:48][CH2:47][C:46](=O)[CH2:45][CH2:44]2)[O:42][CH2:41]1>O1CCCC1>[F:34][C:3]1([F:2])[C:7]([F:8])([F:9])[C:6]2[CH:10]=[CH:11][CH:12]=[C:13]([CH:14]=[C:46]3[CH2:47][CH2:48][C:43]4([O:50][CH2:40][CH2:41][O:42]4)[CH2:44][CH2:45]3)[C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 19705210HCID 19705210, compoundHCID 178418339Butyllithium

Product 1

HCID 197052368-(2,2,3,3-Tetrafluoro-2,3-dihydrobenzofuran-7-ylmethylene)-1,4-dioxaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared in a manner analogous to that of Step B of Example 2, using 20.1 grams (0.039 mole) of (2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran-7-ylmethyl)triphenylphosphonium bromide, 15.4 mL (0.039 mole) of n-butyllithium (2.5M in hexanes), and 5.0 grams (0.032 mole) of 1,4-cyclohexanedione mono-ethylene ketal in about 55 mL of dry tetrahydrofuran, yielding 8-(2,2,3,3-tetrafluoro-2,3-dihydrobenzofuran-7-ylmethylene)-1,4-dioxaspiro[4.5]decane.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step B of Example 2

Sources & evidence

ORD record
ord-3e6932901d4c41ed95d7ad7355a98713
Source dataset
uspto-grants-1996_07
Patent number
US05536725

Reaction notes

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