Hydrochloric Acid → HCID 19386286, compound

HRID 2399213Notes

Reaction equation

HRID 2399213 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][CH:16]3[CH2:25][CH2:24][C:19]4(OCC[O:20]4)[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl>O1CCCC1.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][CH:16]3[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19386519HCID 19386519, compound

Product 1

HCID 19386286HCID 19386286, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.30 g of 8-[(4'-fluoro-4-biphenylyl)ethynyl]-1,4-dioxaspiro[4.5]decane in 30 ml of tetrahydrofuran was stirred with 3.5 ml of 3N hydrochloric acid for 2.4 hours. The reaction mixture was diluted with diethyl ether, washed with saturated sodium hydrogen carbonate solution and with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated. 1.11 g of 4-[(4'-fluoro-4-biphenylyl)ethynyl]cyclohexanone were obtained.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution and with saturated sodium chloride solution
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b3a84772669b4de682c9c80bcf8588d8
Source dataset
uspto-grants-1995_09
Patent number
US05447657

Reaction notes

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