Ethanol → HCID 12834404, compound

HRID 1065268Notes

Reaction equation

HRID 1065268 reaction equation
[Na].CC1C=CC=CC=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2(C#N)[CH2:25][CH2:24][C:19]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1.C(O)C>CO>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:25][CH2:24][C:19]3([O:20][CH2:21][CH2:22][O:23]3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 1140Toluene2×HCID 5360545SodiumHCID 122302421,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-fluorophenyl)-

Product 1

HCID 12834404HCID 12834404, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and hot (±100° C.) mixture of 101 parts of sodium and 450 parts of methylbenzene is added dropwise a solution of 189 parts of 8-(4-fluorophenyl)-1,4-dioxaspiro[4,5]decane-8-carbonitrile in 450 parts of methylbenzene and 100 parts of absolute ethanol (temperature remained at about 90° C.). Then there are added successively and dropwise 260 parts of absolute ethanol and 160 parts of methanol. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto ice-water and the product is extracted with trichloromethane. The extract is washed successively with a hydrochloric acid solution 5%, a sodium bicarbonate solution 5% and with water, dried, filtered and evaporated, yielding 167 parts of 8-(4-fluorophenyl)-1,4-dioxaspiro[4,5]decane; mp. <60° C.

Workup

  1. additionThen there are added successively
  2. stirringUpon completion, stirring
  3. additionThe reaction mixture is poured onto ice-water
  4. extractionthe product is extracted with trichloromethane
  5. washThe extract is washed successively with a hydrochloric acid solution 5%
  6. dry with materiala sodium bicarbonate solution 5% and with water, dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-5fc0e3e463c648b4948ca27a19772b6a
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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