Sulfuric Acid → HCID 13102754, compound

HRID 2164436Notes

Reaction equation

HRID 2164436 reaction equation
[CH3:1][Mg]I.[C:4]([CH:6]([OH:21])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1)#[CH:5].S(=O)(=O)(O)O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.O1CCCC1>[C:4]([CH:6]([OH:21])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH2:1])[CH:8]=1)#[CH:5]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24477Sodium ThiosulfateHCID 13102753HCID 13102753, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 13102754HCID 13102754, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To methyl magnesium iodide (1.4 g) in ether (25 cm3) was added a solution of α-ethynyl-3-benzoylbenzyl alcohol (0.5 g) in ether (10 cm3) with stirring during 10 minutes at 20° C., then the mixture refluxed for 5 minutes and poured onto a mixture of 40% sulphuric acid (40 cm3), sodium thiosulphate (3 g) and tetrahydrofuran (20 cm3). After 16 hours at 20° C., this mixture was extracted with ether (3×150 cm3), washed with sodium thiosulphate solution (2M), saturated sodium chloride, dried and finally evaporated to give the title product, yield 0.48 g (96%) nD20 1.5942.

Workup

  1. temperaturethe mixture refluxed for 5 minutes
  2. waitAfter 16 hours at 20° C.
  3. extractionthis mixture was extracted with ether (3×150 cm3)
  4. washwashed with sodium thiosulphate solution (2M), saturated sodium chloride
  5. customdried
  6. customfinally evaporated

Sources & evidence

ORD record
ord-6edf1932bb9f4bea8c303061014c869b
Source dataset
uspto-grants-1985_03
Patent number
US04504491

Reaction notes

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