Water → HCID 21431782, compound

HRID 436928Notes

Reaction equation

HRID 436928 reaction equation
[CH:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]Br)=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[C-:15]#[N:16].[Na+].O>CN(C)C=O>[CH:1]1([C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:15]#[N:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 21431781HCID 21431781, compound

Product 1

HCID 21431782HCID 21431782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

α-Bromo-p-tolyl cyclobutyl ketone (18.5 g) in dimethylformamide (50 ml) was added during 35 minutes to sodium cyanide (4 g) in dimethylformamide (100 ml) which was cooled below 10° and stirred. The solution was allowed to warm to 20° during 2 hours and poured into water (1 l). The mixture was extracted with ether (3× 200 ml) and the combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was extracted with light petroleum (b.p. 60°-80°) (7× 250 ml) and the extracts were evaporated to leave an oil which partly crystallised on standing.

Workup

  1. temperaturewas cooled below 10°
  2. temperatureto warm to 20° during 2 hours
  3. extractionThe mixture was extracted with ether (3× 200 ml)
  4. dry with materialthe combined extracts were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. extractionThe residue was extracted with light petroleum (b.p. 60°-80°) (7× 250 ml)
  8. customthe extracts were evaporated
  9. customto leave an oil which
  10. custompartly crystallised

Sources & evidence

ORD record
ord-f602f594192c4fd78b96a76cf10b4424
Source dataset
uspto-grants-1977_06
Patent number
US04028404

Reaction notes

Loading…