Diethyl Ether → HCID 19705272, compound

HRID 727192Notes

Reaction equation

HRID 727192 reaction equation
Br[CH:2]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.[F:12][C:13]([F:23])([F:22])[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].[Cl-].[NH4+].C(OCC)C>O1CCCC1>[O:9]1[C:5]2([CH2:10][CH2:11][CH:2]([C:15]3[C:14]([C:13]([F:23])([F:22])[F:12])=[CH:21][CH:20]=[CH:19][C:16]=3[CH2:17][OH:18])[CH2:3][CH2:4]2)[O:6][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 137651298-bromo-1,4-dioxaspiro[4.5]decane

Product 1

HCID 19705272HCID 19705272, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared in a manner analogous to that of Step B of Example 6, using 22.1 grams (0.09 mole) of the Grignard reagent of 8-bromo-1,4-dioxaspiro[4.5]decane and 17.4 grams (0.10 mole) of 3-trifluoromethylbenzaldehyde in tetrahydrofuran. Upon completion of the reaction, the reaction mixture is poured into a mixture of 100 grams of ice, 100 mL of an aqueous solution saturated with ammonium chloride, and 200 mL of diethyl ether. This mixture is filtered and the organic layer is separated. The organic layer is concentrated under reduced pressure, yielding [(1,4-dioxaspiro[4.5]decan-8-yl)(3-trifluoromethylphenyl)]methanol.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step B of Example 6
  2. customUpon completion of the reaction
  3. filtrationThis mixture is filtered
  4. customthe organic layer is separated
  5. concentrationThe organic layer is concentrated under reduced pressure

Sources & evidence

ORD record
ord-1355eb88ccb34aedbf99e406539765fd
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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